Nematocidal sulfonamides

ABSTRACT

Disclosed are compounds of Formula 1, N-oxides, and salts thereof, 
     
       
         
         
             
             
         
       
     
     wherein
         Z is O or S; and   R 1 , R 2 , R 3 , Q and n are as defined in the disclosure.
 
Also disclosed are compositions containing the compounds of Formula 1 and methods for controlling a parasitic nematode comprising contacting the parasitic nematode or its environment with a biologically effective amount of a compound or a composition of the invention.

FIELD OF THE INVENTION

This invention relates to certain sulfonamides, their N-oxides, salts and compositions suitable for agronomic and nonagronomic uses, and methods of their use for controlling parasitic nematodes in both agronomic and nonagronomic environments.

BACKGROUND OF THE INVENTION

The control of plant-parasitic nematodes is extremely important in achieving high crop efficiency. Nematode-induced root damage can cause significant reduction in crop yields and quality and thereby result in increased costs to the consumer. Due to widespread development of resistance to anthelmintic agents in nematode parasites, nematodes continue to cause problems in livestock despite the available chemical therapeutic agents. The need continues for new compounds which are more effective, less costly, less toxic, environmentally safer or have different modes of action.

European Patent Application Publication No. 0 244 166 A2 discloses compounds of Formula i as herbicides

wherein, inter alia, R is H or an organic substituent, W is O or S, L is an aryl or heteroaryl moiety, and A is selected from a list of bi-, tri- and quadricyclic heterocyclic groups.

The compounds of the present invention are not disclosed in this publication.

SUMMARY OF THE INVENTION

This invention is directed to compounds of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, and compositions containing them and their use for controlling a parasitic nematode:

wherein

-   -   Z is O or S;     -   each R¹ is independently halogen, cyano, nitro, SF₅, OCN, SCN,         Si(R¹⁵)₃, OR⁴, NR⁵R⁶, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl,         C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R⁷,         OC(O)OR⁸, OC(O)NR¹¹R¹², OS(O)₂R⁹, OS(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷,         N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹ or N(R¹⁰)S(O)₂NR¹¹R¹²; or C₃-C₇         cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl         or C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and         S(O)_(m)R^(9a); or C₁-C₆ alkyl substituted with 1 to 4         substituents independently selected from the group consisting of         cyano, nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²; or phenyl, naphthalenyl or a 5- or         6-membered heteroaromatic ring, each optionally substituted with         1 to 5 substituents independently selected from the group         consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl,         C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄         haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);     -   R² is H, halogen, cyano, nitro, SF₅, OCN, SCN, Si(R¹⁵)₃, OR⁴,         NR⁵R⁶, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆         haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸,         C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R⁷, OC(O)OR⁸,         OC(O)NR¹¹R¹², OS(O)₂R⁹, OS(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷,         N(R¹⁰)C(O)NR¹¹R¹², N(R¹⁰)S(O)₂R⁹ or N(R¹⁰)S(O)₂NR¹¹R¹²; or C₃-C₇         cycloalkyl, C₄-C₈ cycloalkylalkyl C₆-C₁₄ cycloalkylcycloalkyl or         C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and         S(O)_(m)R^(9a); or C₁-C₆ alkyl substituted with 1 to 4         substituents independently selected from the group consisting of         cyano, nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²; or phenyl, naphthalenyl or a 5- or         6-membered heteroaromatic ring, each optionally substituted with         1 to 5 substituents independently selected from the group         consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl,         C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄         haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);     -   R³ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆         haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸,         C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²; or C₃-C₇ cycloalkyl,         C₄-C₈ cycloalkylalkyl or C₅-C₇ cycloalkenyl, each optionally         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or C₁-C₆ alkyl         substituted with 1 to 4 substituents independently selected from         the group consisting of cyano, nitro, OR⁴, NR⁵R⁶, C(X)R⁷,         C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²; or C₁-C₆         alkyl substituted with 1 or 2 substituents independently         selected from the group consisting of phenyl or a 5- or         6-membered heteroaromatic ring, each optionally substituted with         1 to 5 substituents independently selected from the group         consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl,         C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄         haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a); or         phenyl optionally substituted with 1 to 5 substituents         independently selected from the group consisting of halogen,         cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄         alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl,         C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹²,         OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);     -   Q is phenyl, naphthalenyl, a 5- or 6-membered heteroaromatic         ring or an 8- to 10-membered heteroaromatic bicyclic ring         system, each optionally substituted with 1 to 5 substituents         independently selected from the group consisting of halogen,         cyano, nitro, SF₅, OCN, SCN, Si(R¹⁵)₃, OR⁴, NR⁵R⁶, C₁-C₆ alkyl,         C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆         alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹²,         S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R⁷, OC(O)OR⁸, OC(O)NR¹¹R¹²,         OS(O)₂R⁹, OS(O)₂NR¹¹R¹², N(R¹⁰)C(O)R⁷, N(R¹⁰)C(O)NR¹¹R¹²,         N(R¹⁰)S(O)₂R⁹, N(R¹⁰)S(O)₂NR¹¹R¹² and R¹⁴;     -   each X is independently O or S;     -   each R⁴ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₁-C₆ alkyl, C₂-C₆ alkenyl or C₂-C₆ alkynyl, each substituted         with 1 to 4 substituents independently selected from the group         consisting of cyano, nitro, OR^(4a), NR^(5a)R^(6a), C(X)R^(7a),         C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) or S(O)₂NR¹¹R¹²; or         phenyl optionally substituted with 1 to 3 substituents         independently selected from the group consisting of halogen,         cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄         haloalkyl, C₂-C₄ haloalkenyl, C(X)R^(7a), C(O)OR^(8a),         C(O)NR¹¹R¹², OR^(4a), C₂-C₆ alkoxyalkyl, S(O)_(m)R^(9a),         S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);     -   each R^(4a) is independently H, C₁-C₆ alkyl or C₁-C₆ haloalkyl;     -   each R⁵ is independently H, NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆         haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl,         C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or         S(O)₂NR¹¹R¹²; or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl or C₅-C₇ cycloalkenyl, each optionally         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or phenyl         optionally substituted with 1 to 3 substituents independently         selected from the group consisting of halogen, cyano, nitro,         C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl,         C₂-C₄ haloalkenyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹²,         OR^(4a), C₂-C₆ alkoxyalkyl, S(O)_(m)R^(9a), S(O)₂NR¹¹R¹²,         NR^(5a)R^(6a), OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);     -   each R^(5a) is independently H or C₁-C₆ alkyl;     -   each R⁶ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl or C₅-C₇ cycloalkenyl, each optionally         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a);     -   each R^(6a) is independently H, C₁-C₆ alkyl, C(O)R¹³ or         C(O)OR¹³;     -   each R⁷ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl or C₅-C₇ cycloalkenyl, each optionally         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or phenyl         optionally substituted with 1 to 3 substituents independently         selected from the group consisting of halogen, cyano, nitro,         C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl,         C₂-C₄ haloalkenyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹²,         OR^(4a), C₂-C₆ alkoxyalkyl, S(O)_(m)R^(9a), S(O)₂NR¹¹R¹²,         NR^(5a)R^(6a), OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);     -   each R^(7a) is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl;     -   each R⁸ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl or C₅-C₇ cycloalkenyl, each optionally         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or C₁-C₆ alkyl,         C₂-C₆ alkenyl or C₂-C₆ alkynyl, each substituted with 1 to 4         substituents independently selected from the group consisting of         cyano, nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²; or phenyl optionally substituted         with 1 to 3 substituents independently selected from the group         consisting of halogen, cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl,         C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C(X)R^(7a),         C(O)OR^(8a), C(O)NR¹¹R¹², OR^(4a), C₂-C₆ alkoxyalkyl,         S(O)_(m)R^(9a), S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and         N(R¹⁰)C(O)R^(7a);     -   each R^(8a) is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl;     -   each R⁹ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl or C₅-C₇ cycloalkenyl, each optionally         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or C₁-C₆ alkyl,         C₂-C₆ alkenyl or C₂-C₆ alkynyl, each substituted with 1 to 4         substituents independently selected from the group consisting of         cyano, nitro, OR⁴, NR⁵R⁶, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²; or phenyl optionally substituted         with 1 to 3 substituents independently selected from the group         consisting of halogen, cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl,         C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C(X)R^(7a),         C(O)OR^(8a), C(O)NR¹¹R¹², OR^(4a), C₂-C₆ alkoxyalkyl,         S(O)_(m)R^(9a), S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and         N(R¹⁰)C(O)R^(7a);     -   each R^(9a) is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl;     -   each R¹⁰ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl,         C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) or         S(O)₂NR¹¹R¹²;     -   each R^(10a) is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl,         C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆         haloalkynyl;     -   each R¹¹ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl or C₅-C₇ cycloalkenyl, each optionally         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or C₁-C₆ alkyl,         C₂-C₆ alkenyl or C₂-C₆ alkynyl, each substituted with 1 to 4         substituents independently selected from the group consisting of         cyano, nitro, OR^(4a), NR^(5a)R^(6a), C(X)R^(7a), C(O)OR^(8a),         C(O)NR^(11a)R¹², S(O)_(m)R^(9a) or S(O)₂NR^(11a)R¹²; or phenyl         optionally substituted with 1 to 3 substituents independently         selected from the group consisting of halogen, cyano, nitro,         C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl,         C₂-C₄ haloalkenyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR^(11a)R¹²,         OR^(4a), C₂-C₆ alkoxyalkyl, S(O)_(m)R^(9a), S(O)₂NR^(11a)R¹²,         NR^(5a)R^(6a), OC(O)R^(7a) and N(R^(10a))C(O)R^(7a);     -   each R^(11a) is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl or         C₂-C₆ alkynyl;     -   each R¹² is independently H, NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆         haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl,         C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or         S(O)₂NR¹¹R¹²; or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl or C₅-C₇ cycloalkenyl, each optionally         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or phenyl         optionally substituted with 1 to 3 substituents independently         selected from the group consisting of halogen, cyano, nitro,         C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl,         C₂-C₄ haloalkenyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹²,         OR^(4a), C₂-C₆ alkoxyalkyl, S(O)_(m)R^(9a), S(O)₂NR¹¹R¹²,         NR^(5a)R^(6a), OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);     -   each R¹³ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄         cycloalkylcycloalkyl or C₅-C₇ cycloalkenyl, each optionally         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a);     -   each R¹⁴ is independently C₃-C₇ cycloalkyl, C₄-C₈         cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl or C₅-C₇         cycloalkenyl, each optionally substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and         S(O)_(m)R^(9a); or C₁-C₆ alkyl, C₂-C₆ alkenyl or C₂-C₆ alkynyl,         each substituted with 1 to 4 substituents independently selected         from the group consisting of cyano, nitro, OR⁴, NR⁵R⁶, C(X)R⁷,         C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²; or phenyl,         naphthalenyl or a 5- or 6-membered heteroaromatic ring, each         optionally substituted with 1 to 5 substituents independently         selected from the group consisting of halogen, cyano, nitro,         OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄         haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷,         C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and         N(R¹⁰)C(O)R^(7a);     -   each R¹⁵ is independently C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₅-C₇         cycloalkenyl, each optionally substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and         S(O)_(m)R^(9a); or phenyl optionally substituted with 1 to 5         substituents independently selected from the group consisting of         halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl,         C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆         alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹,         S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);     -   each m is independently 0, 1 or 2; and     -   n is 0, 1, 2, 3 or 4.

This invention is also directed to such compounds of Formula 1 (including all stereoisomers), N-oxides, and salts thereof, and compositions containing them and their use for controlling a parasitic nematode as described above, and further herein, provided that when n is 2 and one R¹ is CF₃ in the 3-position of Formula 1 and the other R¹ is Cl in the 5-position of Formula 1, and R² and R³ are H, then Q is other than 2-chlorophenyl, 2-chloro-6-methylphenyl, 2,6-dichlorophenyl, 2-chloro-4-fluorophenyl, 2,5-bis(2,2,2-trifluoroethoxy)phenyl, 2,4,6-trichlorophenyl, 2-chloro-5-(trifluoromethyl)phenyl or 3,5-dimethyl-4-isoxazolyl.

This invention also provides a composition comprising a compound of Formula 1, an N-oxide, or a salt thereof, and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents. In one embodiment, this invention also provides a composition for controlling a parasitic nematode comprising a compound of Formula 1, an N-oxide, or a salt thereof, and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, said composition optionally further comprising at least one additional biologically active compound or agent.

This invention provides a method for controlling a parasitic nematode comprising contacting the parasitic nematode or its environment with a biologically effective amount of a compound of Formula 1, an N-oxide, or a salt thereof, (e.g., as a composition described herein). This invention also relates to such method wherein the parasitic nematode or its environment is contacted with a composition comprising a biologically effective amount of a compound of Formula 1, an N-oxide, or a salt thereof, and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, said composition optionally further comprising a biologically effective amount of at least one additional biologically active compound or agent.

This invention also provides a method for protecting a seed from a parasitic nematode comprising contacting the seed with a biologically effective amount of a compound of Formula 1, an N-oxide, or a salt thereof, (e.g., as a composition described herein). This invention also relates to the treated seed.

DETAILS OF THE INVENTION

As used herein, the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having”, “contains”, “containing”, “characterized by” or any other variation thereof, are intended to cover a non-exclusive inclusion, subject to any limitation explicitly indicated.

For example, a composition, mixture, process or method that comprises a list of elements is not necessarily limited to only those elements but may include other elements not expressly listed or inherent to such composition, mixture, process or method.

The transitional phrase “consisting of” excludes any element, step or ingredient not specified. If in the claim, such would close the claim to the inclusion of materials other than those recited except for impurities ordinarily associated therewith. When the phrase “consisting of” appears in a clause of the body of a claim, rather than immediately following the preamble, it limits only the element set forth in that clause; other elements are not excluded from the claim as a whole.

The transitional phrase “consisting essentially of” is used to define a composition or method that includes materials, steps, features, components or elements, in addition to those literally disclosed, provided that these additional materials, steps, features, components or elements do not materially affect the basic and novel characteristic(s) of the claimed invention. The term “consisting essentially of” occupies a middle ground between “comprising” and “consisting of”.

Where applicants have defined an invention or a portion thereof with an open-ended term such as “comprising”, it should be readily understood that (unless otherwise stated) the description should be interpreted to also describe such an invention using the terms “consisting essentially of” or “consisting of”.

Further, unless expressly stated to the contrary, “or” refers to an inclusive or and not to an exclusive or. For example, a condition A or B is satisfied by any one of the following: A is true (or present) and B is false (or not present), A is false (or not present) and B is true (or present), and both A and B are true (or present).

Also, the indefinite articles “a” and “an” preceding an element or component of the invention are intended to be nonrestrictive regarding the number of instances (i.e. occurrences) of the element or component. Therefore “a” or “an” should be read to include one or at least one, and the singular word form of the element or component also includes the plural unless the number is obviously meant to be singular.

As used to in the present disclosure and claims, the term “nematode” refers to a living organism of the Phylum Nematoda. As generally defined, a “parasite” lives or grows inside or feeds on another living organism (such as a plant, animal or human) described as the “host”. As referred to in the present disclosure and claims a “parasitic nematode” is particularly a nematode that injures or damages tissue or causes other forms of disease in plants, animals (particularly vertebrates) or humans.

A parasite “infestation” refers to the presence of parasites in numbers that pose a risk to plants, humans or animals. The presence can be in the environment, e.g., in a human or animal house, or surrounding property or structures, on an agricultural crop or other type of plant, in animal bedding, on the skin or fur of an animal, etc. When the infestation that is referred to is within an animal, e.g., in the blood or other internal tissues, the term infestation is also intended to be synonymous with the term, “infection,” as that term is generally understood in the art, unless otherwise stated.

As referred to in the present disclosure and claims, the terms “parasiticidal” and “parasiticidally” refers to observable effects on a parasitic nematode to provide protection of a plant, animal or human from the nematode. Parasiticidal effects typically relate to diminishing the occurrence or activity of the target parasitic nematode. Such effects on the nematode include necrosis, death, retarded growth, diminished mobility or lessened ability to remain on or in the host plant, animal or human, reduced feeding and inhibition of reproduction. These effects on parasitic nematodes provide control (including prevention, reduction or elimination) of parasitic infestation or infection of the plant, animal or human. Therefore “control” of a parasitic nematode means achieving a parasiticidal effect on the nematode. The expressions “parasiticidally effective amount” and “biologically effective amount” in the context of applying a chemical compound to control a parasitic nematode refer an amount of the compound that is sufficient to control the parasitic nematode.

The term “agronomic” refers to the production of field crops such as for food and fiber and includes the growth of soybeans and other legumes, cereal (e.g., wheat, oats, barley, rye, rice, maize/corn), leafy vegetables (e.g., lettuce, cabbage, and other cole crops), fruiting vegetables (e.g., tomatoes, pepper, eggplant, crucifers and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g., pome, stone and citrus), small fruit (berries, cherries) and other specialty crops (e.g., canola, sunflower, olives).

The term “nonagronomic” refers to other than field crops, such as horticultural crops (e.g., greenhouse, nursery or ornamental plants not grown in a field), residential, agricultural, commercial and industrial structures, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored product, agro-forestry and vegetation management, public health (i.e. human) and animal health (e.g., domesticated animals such as pets, livestock and poultry, undomesticated animals such as wildlife) applications.

Nonagronomic applications include protecting an animal from a parasitic nematode by administering a parasiticidally effective (i.e. biologically effective) amount of a compound of the invention, typically in the form of a composition formulated for veterinary use, to the animal to be protected.

In the above recitations, the term “alkyl”, used either alone or in compound words such as “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. “Alkenyl” includes straight-chain or branched alkenes such as ethenyl, 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as ethynyl, 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl.

“Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂.

“Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl. The term “cycloalkylalkyl” denotes cycloalkyl substitution on an alkyl moiety. Examples of “cycloalkylalkyl” include cyclopropylmethyl, cyclopentylethyl, and other cycloalkyl moieties bonded to straight-chain or branched alkyl groups. “Cycloalkenyl” includes groups such as cyclopentenyl and cyclohexenyl as well as groups with more than one double bond such as 1,3- and 1,4-cyclohexadienyl. The term “cycloalkylcycloalkyl” denotes cycloalkyl substitution on another cycloalkyl ring, wherein each cycloalkyl ring independently has from 3 to 7 carbon atom ring members. Examples of cycloalkylcycloalkyl include cyclopropylcyclopropyl (such as 1,1′-bicyclopropyl-1-yl, 1,1′-bicyclopropyl-2-yl), cyclohexylcyclopentyl (such as 4-cyclopentylcyclohexyl) and cyclohexylcyclohexyl (such as 1,1′-bicyclohexyl-1-yl), and the different cis- and trans-cycloalkylcycloalkyl isomers, (such as (1R,2S)-1,1′-bicyclopropyl-2-yl and (1R,2R)-1,1′-bicyclopropyl-2-yl).

The term “halogen”, either alone or in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” includes fluorine, chlorine, bromine or iodine. Further, when used in compound words such as “haloalkyl”, or when used in descriptions such as “alkyl substituted with halogen” said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” or “alkyl substituted with halogen” include F₃C, ClCH₂, CF₃CH₂ and CF₃CCl₂. The terms “haloalkoxy”, “haloalkenyl”, “haloalkynyl”, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkoxy” include CF₃O, CCl₃CH₂O, HCF₂CH₂CH₂O and CF₃CH₂O. Examples of “haloalkenyl” include (Cl)₂C═CHCH₂ and CF₃CH₂CH═CHCH₂. Examples of “haloalkynyl” include HC≡CCHCl, CF₃C≡C, CCl₃C≡C and FCH₂C≡CCH₂.

The chemical abbreviation C(O) as used herein represents a carbonyl moiety. For example, C(O)CH₃ represents an acetyl group. The chemical abbreviations CO₂ and C(O)O as used herein represent an ester moiety. For example, CO₂Me and C(O)OMe represent a methyl ester.

“OCN” means —O—C≡N, and “SCN” means —S—C≡N.

The total number of carbon atoms in a substituent group is indicated by the “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 14. C₂ alkoxyalkyl designates CH₃OCH₂; C₃ alkoxyalkyl designates, for example, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; and C₄ alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH₃CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂.

When a compound is substituted with a substituent bearing a subscript that indicates the number of said substituents can exceed 1, said substituents (when they exceed 1) are independently selected from the group of defined substituents, e.g., R¹, n is 0, 1, 2, 3 or 4. When a group contains a substituent which can be hydrogen, for example R² or R³, then when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted. When a variable group is shown to be optionally attached to a position, for example (R^(v))_(r) in U-29 of Exhibit 1 wherein r may be 0, then hydrogen may be at the position even if not recited in the variable group definition. When one or more positions on a group are said to be “not substituted” or “unsubstituted”, then hydrogen atoms are attached to take up any free valency.

Unless otherwise indicated, a “ring” or “ring system” as a component of Formula 1 (e.g., substituent Q) is carbocyclic or heterocyclic. The term “ring system” denotes two or more fused rings. The term “heterocyclic ring” denotes a ring in which at least one atom forming the ring backbone is not carbon, e.g., nitrogen, oxygen or sulfur. Typically a heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. Unless otherwise indicated, a heterocyclic ring can be a saturated, partially unsaturated, or fully unsaturated ring. The term “heterocyclic ring system” denotes a ring system in which at least one ring of the ring system is a heterocyclic ring. Unless otherwise indicated, heterocyclic rings and ring systems can be attached through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

“Aromatic” indicates that each of the ring atoms is essentially in the same plane and has a p-orbital perpendicular to the ring plane, and in which (4n+2) π electrons, where n is a positive integer, are associated with the ring to comply with Hückel's rule. When a fully unsaturated heterocyclic ring satisfies Hückel's rule, then said ring is also called a “heteroaromatic ring”. The term “heteroaromatic ring system” denotes a heterocyclic ring system in which at least one ring of the ring system is aromatic.

As used herein, the following definitions shall apply unless otherwise indicated. The term “optionally substituted” is used interchangeably with the phrase “substituted or unsubstituted” or with the term “(un)substituted”. The expression “optionally substituted with 1 to 4 substituents” means that no substituent is present (i.e. unsubstituted) or that 1, 2, 3 or 4 substituents are present (limited by the number of available bonding positions). Unless otherwise indicated, an optionally substituted group may have a substituent at each substitutable position of the group, and each substitution is independent of the other.

When a substituent is a 5- or 6-membered nitrogen-containing heteroaromatic ring, it may be attached to the remainder of Formula 1 though any available carbon or nitrogen ring atom, unless otherwise described.

An example of phenyl optionally substituted with one to five substituents is the ring illustrated as U-1 in Exhibit 1, wherein R^(v) is as defined in the Summary of the Invention for R¹, R², R³ or Q and r is an integer from 0 to 5.

Examples of an optionally substituted 5- or 6-membered heteroaromatic ring include the rings U-2 through U-61 illustrated in Exhibit 1 wherein R^(v) is any substituent as defined in the Summary of the Invention for R¹, R², R³ or Q and r is an integer from 0 to 4, limited by the number of available positions on each U group. As U-29, U-30, U-36, U-37, U-38, U-39, U-40, U-41, U-42 and U-43 have only one available position, for these U groups r is limited to the integers 0 or 1, and r being 0 means that the U group is unsubstituted and a hydrogen is present at the position indicated by (R^(v))_(r).

As noted above, Q can be (among others) an 8- to 10-membered heteroaromatic bicyclic ring system optionally substituted with substituents selected from a group of substituents as defined in the Summary of Invention. Examples of optionally substituted 8-, 9- or 10-membered heteroaromatic bicyclic ring systems include the rings U-81 through U-123 illustrated in Exhibit 3 wherein R^(v) is any substituent as defined in the Summary of the Invention for Q, and r is typically an integer from 0 to 4.

Although R^(v) groups are shown in the structures U-1 through U-123, it is noted that they do not need to be present since they are optional substituents. The nitrogen atoms that require substitution to fill their valence are substituted with H or R^(v). Note that when the attachment point between (R^(v))_(r) and the U group is illustrated as floating, (R^(v))_(r) can be attached to any available carbon atom or nitrogen atom of the U group. Note that when the attachment point on the U group is illustrated as floating, the U group can be attached to the remainder of Formula 1 through any available carbon or nitrogen of the U group by replacement of a hydrogen atom. Note that some U groups can only be substituted with less than 4 R^(v) groups (e.g., U-2 through U-5, U-7 through U-48, and U-52 through U-61).

A wide variety of synthetic methods are known in the art to enable preparation of aromatic and nonaromatic heterocyclic rings and ring systems; for extensive reviews see the eight volume set of Comprehensive Heterocyclic Chemistry, A. R. Katritzky and C. W. Rees editors-in-chief, Pergamon Press, Oxford, 1984 and the twelve volume set of Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees and E. F. V. Scriven editors-in-chief, Pergamon Press, Oxford, 1996.

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. The compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers or as an optically active form.

Compounds selected from Formula 1, (including all stereoisomers, N-oxides, and salts thereof), typically exist in more than one form, and Formula 1 thus includes all crystalline and non-crystalline forms of the compounds that Formula 1 represents. Non-crystalline forms include embodiments which are solids such as waxes and gums as well as embodiments which are liquids such as solutions and melts. Crystalline forms include embodiments which represent essentially a single crystal type and embodiments which represent a mixture of polymorphs (i.e. different crystalline types). The term “polymorph” refers to a particular crystalline form of a chemical compound that can crystallize in different crystalline forms, these forms having different arrangements and/or conformations of the molecules in the crystal lattice. Although polymorphs can have the same chemical composition, they can also differ in composition due the presence or absence of co-crystallized water or other molecules, which can be weakly or strongly bound in the lattice. Polymorphs can differ in such chemical, physical and biological properties as crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate and biological availability. One skilled in the art will appreciate that a polymorph of a compound represented by Formula 1 can exhibit beneficial effects (e.g., suitability for preparation of useful formulations, improved biological performance) relative to another polymorph or a mixture of polymorphs of the same compound represented by Formula 1. Preparation and isolation of a particular polymorph of a compound represented by Formula 1 can be achieved by methods known to those skilled in the art including, for example, crystallization using selected solvents and temperatures.

One skilled in the art will appreciate that not all nitrogen-containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen-containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and 3-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethyldioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-20, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 149-161, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.

One skilled in the art recognizes that because in the environment and under physiological conditions salts of chemical compounds are in equilibrium with their corresponding nonsalt forms, salts share the biological utility of the nonsalt forms. Thus a wide variety of salts of the compounds of Formula 1 are useful for control of parasitic nematodes. The salts of the compounds of Formula 1 include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids. When a compound of Formula 1 contains an acidic moiety such as a carboxylic acid, phenol or sulfonylamide (i.e. when R³ is H), salts also include those formed with organic or inorganic bases such as pyridine, triethylamine or ammonia, or amides, hydrides, hydroxides or carbonates of sodium, potassium, lithium, calcium, magnesium or barium. Accordingly, the present invention comprises compounds selected from Formula 1, N-oxides and salts thereof.

Embodiments of the present invention as described in the Summary of the Invention include those described below. In the following Embodiments, Formula 1 includes stereoisomers, N-oxides, and salts thereof, and reference to “a compound of Formula 1” includes the definitions of substituents specified in the Summary of the Invention unless further defined in the Embodiments.

Embodiment 1

A compound of Formula 1 wherein Z is O.

Embodiment 2

A compound of Formula 1 wherein Z is S.

Embodiment 3

A compound of Formula 1 or Embodiment 1 or 2 wherein each R¹ is independently halogen, cyano, nitro, OR⁴, C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment 3a

A compound of Embodiment 3 wherein each R¹ is independently halogen, C₁-C₆ haloalkyl or C₁-C₆ haloalkoxy (i.e. OR⁴ and R⁴ is C₁-C₆ haloalkyl).

Embodiment 3b

A compound of Embodiment 3a wherein n is 2, and one R¹ is in the 3-position of Formula 1, and a second R¹ is in the 5-position of Formula 1. Embodiment 3c

A compound of Embodiment 3a or 3b wherein each R¹ is independently halogen or C₁-C₂ haloalkyl.

Embodiment 3d

A compound of Embodiment 3c wherein each R¹ is independently F, Cl, Br or CF₃.

Embodiment 3e

A compound of Embodiment 3c wherein n is 2, and each R¹ is

independently F, Cl, Br or CF₃.

Embodiment 3f

A compound of Formula 1 wherein n is 1, and R¹ is CF₃ and is in the 3-position of Formula 1.

Embodiment 3g

A compound of Formula 1 wherein n is 2, and one R¹ is CF₃ and is in the 3-position of Formula 1, and a second R¹ is Cl and is in the 5-position of Formula 1.

Embodiment 3h

A compound of Formula 1 wherein n is 2, and one R¹ is CF₃ and is in the 3-position of Formula 1, and a second R¹ is Br and is in the 5-position of Formula 1.

Embodiment 3i

A compound of Formula 1 wherein n is 2, and one R¹ is CF₃ and is in the 3-position of Formula 1, and a second R¹ is F and is in the 5-position of Formula 1.

Embodiment 4

A compound of Formula 1 or any of Embodiments 1-31 wherein Q is phenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 4a

A compound of Embodiment 4 wherein Q is phenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, OR^(4a), C₁-C₃ alkyl, C₁-C₃ haloalkyl and C(O)R^(7b);

-   -   each R^(4a) is independently C₁-C₃ alkyl or C₁-C₃ haloalkyl; and     -   each R^(7b) is independently C₁-C₃ alkyl.

Embodiment 4b

A compound of Embodiment 4 wherein Q is phenyl, pyridinyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, furanyl or thienyl, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹² OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 4c

A compound of Embodiment 4b wherein Q is phenyl, pyridinyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl, furanyl or thienyl, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, OR^(4a), C₁-C₃ alkyl and C₁-C₃ haloalkyl; and

-   -   each R^(4a) is independently C₁-C₃ alkyl or C₁-C₃ haloalkyl.

Embodiment 4d

A compound of Embodiment 4b wherein Q is phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 4e

A compound of Embodiment 4d wherein Q is phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, OR^(4a), C₁-C₃ alkyl, C₁-C₃ haloalkyl and C(O)R^(7b);

-   -   each R^(4a) is independently C₁-C₃ alkyl or C₁-C₃ haloalkyl; and     -   each R^(7b) is independently C₁-C₃ alkyl.

Embodiment 4f

A compound of Embodiment 4b wherein Q is pyridinyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 4g

A compound of Embodiment 4f wherein Q is pyridinyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, OR^(4a), C₁-C₃ alkyl and C₁-C₃ haloalkyl; and

-   -   each R^(4a) is independently C₁-C₃ alkyl or C₁-C₃ haloalkyl.

Embodiment 4h

A compound of Embodiment 4b wherein Q is pyrazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 41

A compound of Embodiment 4h wherein Q is pyrazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, OR^(4a), C₁-C₃ alkyl and C₁-C₃ haloalkyl; and

-   -   each R^(4a) is independently C₁-C₃ alkyl or C₁-C₃ haloalkyl.

Embodiment 4j

A compound of Embodiment 4b wherein Q is oxazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 4k

A compound of Embodiment 4j wherein Q is oxazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, OR^(4a), C₁-C₃ alkyl and C₁-C₃ haloalkyl; and

-   -   each R^(4a) is independently C₁-C₃ alkyl or C₁-C₃ haloalkyl.

Embodiment 4l

A compound of Embodiment 4b wherein Q is thiazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 4m

A compound of Embodiment 41 wherein Q is thiazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, OR^(4a), C₁-C₃ alkyl and C₁-C₃ haloalkyl; and

-   -   each R^(4a) is independently C₁-C₃ alkyl or C₁-C₃ haloalkyl.

Embodiment 4n

A compound of Embodiment 4b wherein Q is isoxazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 4o

A compound of Embodiment 4n wherein Q is isoxazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, OR^(4a), C₁-C₃ alkyl and C₁-C₃ haloalkyl; and

-   -   each R^(4a) is independently C₁-C₃ alkyl or C₁-C₃ haloalkyl.

Embodiment 4p

A compound of Embodiment 4b wherein Q is isothiazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 4q

A compound of Embodiment 4p wherein Q is isothiazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, OR^(4a), C₁-C₃ alkyl and C₁-C₃ haloalkyl; and

-   -   each R^(4a) is independently C₁-C₃ alkyl or C₁-C₃ haloalkyl.

Embodiment 4r

A compound of Embodiment 4b wherein Q is furanyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 4s

A compound of Embodiment 4r wherein Q is furanyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, OR^(4a), C₁-C₃ alkyl and C₁-C₃ haloalkyl; and

-   -   each R^(4a) is independently C₁-C₃ alkyl or C₁-C₃ haloalkyl.

Embodiment 4t

A compound of Embodiment 4b wherein Q is thienyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 4u

A compound of Embodiment 4t wherein Q is thienyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, OR^(4a), C₁-C₃ alkyl and C₁-C₃ haloalkyl; and

-   -   each R^(4a) is independently C₁-C₃ alkyl or C₁-C₃ haloalkyl.

Embodiment 4v

A compound of Embodiment 4b wherein Q is phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C(X)R⁷ and C(O)OR⁸.

Embodiment 4w

A compound of Embodiment 4b wherein Q is pyridinyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C(X)R⁷ and C(O)OR⁸.

Embodiment 4x

A compound of Embodiment 4b wherein Q is furanyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C(X)R⁷ and C(O)OR⁸.

Embodiment 5

A compound of Formula 1 or any of Embodiments 1-4x wherein R² is H, halogen or C₁-C₆ alkyl.

Embodiment 5a

A compound of Embodiment 5 wherein R² is H, F, Cl, Br or C₁-C₂ alkyl.

Embodiment 5b

A compound of Embodiment 5a wherein R² is H, Cl, Br or CH₃.

Embodiment 5c

A compound of Embodiment 5a wherein R² is H.

Embodiment 6

A compound of Formula 1 or any of Embodiments 1-5c wherein R³ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C(X)R⁷, C(O)OR⁸ or S(O)_(m)R⁹; or C₁-C₆ alkyl substituted with 1 or 20R⁴.

Embodiment 6a

A compound of Embodiment 6 wherein R³ is H or C₁-C₆ alkyl.

Embodiment 6b

A compound of Embodiment 6a wherein R³ is H.

Embodiment 7

A compound of Formula 1 or any of Embodiments 1-6b wherein R⁴ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl; or C₁-C₆ alkyl, C₂-C₆ alkenyl or C₂-C₆ alkynyl, each substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, OR^(4a), NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) or S(O)₂NR¹¹R¹².

Embodiment 8

A compound of Formula 1 or any of Embodiments 1-7 wherein R⁵ is H, NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²; or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl or C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a)

Embodiment 9

A compound of Formula 1 or any of Embodiments 1-8 wherein R⁶ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl or C₂-C₆ alkynyl; or C₃-C₇ cycloalkyl or C₄-C₈ cycloalkylalkyl, each optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl and OR^(4a);

Embodiment 10

A compound of Formula 1 or any of Embodiments 1-9 wherein R⁷ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl; or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl or C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

Embodiment 11

A compound of Formula 1 or any of Embodiments 1-10 wherein R⁸ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl; or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl, C₆-C₁₄ cycloalkylcycloalkyl or C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or C₁-C₆ alkyl substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, OR^(4a), NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) or S(O)₂NR¹¹R¹².

Embodiment 12

A compound of Formula 1 or any of Embodiments 1-11 wherein R⁹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl; or C₁-C₆ alkyl substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, OR^(4a), NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) or S(O)₂NR¹¹R¹².

Embodiment 13

A compound of Formula 1 or any of Embodiments 1-12 wherein R¹⁰ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl or C₂-C₆ alkynyl.

Embodiment 14

A compound of Formula 1 or any of Embodiments 1-13 wherein R¹⁴ is C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or C₁-C₆ alkyl substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹².

Embodiments of this invention, including Embodiments 1-14 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1 but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1. In addition, embodiments of this invention, including Embodiments 1-14 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.

Combinations of Embodiments 1-14 are illustrated by:

Embodiment A

A compound of Formula 1 wherein

-   -   Z is O; and     -   Q is phenyl or a 5- or 6-membered heteroaromatic ring, each         optionally substituted with 1 to 3 substituents independently         selected from the group consisting of halogen, cyano, nitro,         OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄         haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷,         C(O)OR⁸, C(X)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and         N(R¹⁰)C(O)R^(7a).

Embodiment B

A compound of Embodiment A wherein

-   -   Q is phenyl, pyridinyl, pyrazolyl, oxazolyl, thiazolyl,         isoxazolyl, isothiazolyl, furanyl or thienyl, each optionally         substituted with 1 to 3 substituents independently selected from         the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄         alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄         haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(X)NR¹¹R¹²,         S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment C

A compound of Embodiment B wherein

-   -   each R¹ is independently halogen, cyano, nitro, OR⁴, C₁-C₆ alkyl         or C₁-C₆ haloalkyl;     -   R² is H, halogen or C₁-C₆ alkyl;     -   R³ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C(X)R⁷, C(O)OR⁸ or         S(O)_(m)R⁹; or C₁-C₆ alkyl substituted with 1 or 20R⁴; and     -   n is 1 or 2.

Specific embodiments include compounds of Formula 1 selected from the group consisting of:

-   8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide, -   8-chloro-N-[(4-cyano-2,5-dimethylphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide, -   N-[(5-acetyl-2-chlorophenyl)sulfonyl]-8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide, -   8-chloro-N-[(3-methyl-2-thienyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide, -   8-chloro-N-[(4-methyl-2-thienyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide, -   8-chloro-N-[(3-chloro-1-methyl-1H-pyrazol-4-yl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide, -   8-chloro-N-[(5-methoxy-2-nitrophenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide, -   8-chloro-N-[(2-chloro-5-ethylphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide, -   8-chloro-N-[(1-ethyl-3-methyl-1H-pyrazol-4-yl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide, -   8-bromo-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide, -   N-[(2-bromo-5-methylphenyl)sulfonyl]-8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide, -   8-chloro-N-[(2-chloro-5-methylphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide, -   8-chloro-N-[(3-chloro-1-ethyl-1H-pyrazol-4-yl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide,     and -   N-[(5-acetyl-2-methylphenyl)sulfonyl]-8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide.

Further embodiments of the present invention as described in the Summary of the Invention include those described below. In the following Embodiments, Formula 1p includes stereoisomers, N-oxides, and salts thereof, and reference to “a compound of Formula 1p” includes the definitions of substituents specified in the Summary of the Invention unless further defined in the Embodiments.

Embodiment 15

A compound of Formula 1p

wherein

-   -   Z is O or S;     -   each R¹ is independently halogen, cyano, nitro, OR⁴, NR⁵R⁶,         C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl,         C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) or N(R¹⁰)C(O)R^(7a); or         C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₅-C₇ cycloalkenyl,         each optionally substituted with 1 to 4 substituents         independently selected from the group consisting of halogen,         cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and         S(O)_(m)R^(9a); or C₁-C₆ alkyl substituted with halogen, cyano,         nitro, OR⁴, NR⁵R⁶, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl,         C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷,         C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²; or phenyl,         naphthalenyl or a 5- or 6-membered heteroaromatic ring, each         optionally substituted with 1 to 5 substituents independently         selected from the group consisting of halogen, cyano, nitro,         OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄         haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷,         C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and         N(R¹⁰)C(O)R^(7a);     -   R² is H, halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆ alkyl, C₁-C₆         haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl,         C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or         S(O)₂NR¹¹R¹²; or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or         C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and         S(O)_(m)R^(9a); or C₁-C₆ alkyl substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆ alkyl, C₁-C₆ haloalkyl,         C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆         haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ and         S(O)₂NR¹¹R¹²;     -   R³ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆         haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸,         C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²; or C₃-C₇ cycloalkyl,         C₄-C₈ cycloalkylalkyl or C₅-C₇ cycloalkenyl, each optionally         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or C₁-C₆ alkyl         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆         alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆         alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²; or phenyl optionally substituted         with 1 to 5 substituents independently selected from the group         consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl,         C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄         haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);     -   Q is phenyl, naphthalenyl, a 5- or 6-membered heteroaromatic         ring or an 8- to 10-membered heteroaromatic bicyclic ring         system, each optionally substituted with 1 to 5 substituents         independently selected from the group consisting of halogen,         cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl,         C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹²,         OC(O)R^(7a), N(R¹⁰)C(O)R^(7a) and R¹⁴;     -   each X is independently O or S;     -   each R⁴ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₁-C₆ alkyl substituted with 1 to 4 substituents         independently selected from the group consisting of halogen,         cyano, nitro, OR^(4a), NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆         haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl,         C₂-C₆ haloalkynyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹²,         S(O)_(m)R^(9a) or S(O)₂NR¹¹R¹²; or phenyl optionally substituted         with 1 to 3 substituents independently selected from the group         consisting of halogen, cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl,         C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C(X)R^(7a),         C(O)OR^(8a), C(O)NR¹¹R¹², OR^(4a), C₂-C₆ alkoxyalkyl,         S(O)_(m)R^(9a), S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and         N(R¹⁰)C(O)R^(7a);     -   each R^(4a) is independently H, C₁-C₆ alkyl or C₁-C₆ haloalkyl;     -   each R⁵ is independently H, NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆         haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl,         C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or         S(O)₂NR¹¹R¹²; or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or         C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and         S(O)_(m)R^(9a); or phenyl optionally substituted with 1 to 3         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄         alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C(X)R^(7a),         C(O)OR^(8a), C(O)NR¹¹R¹², OR^(4a), C₂-C₆ alkoxyalkyl,         S(O)_(m)R^(9a), S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and         N(R¹⁰)C(O)R^(7a);     -   each R^(5a) is independently H or C₁-C₆ alkyl;     -   each R⁶ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₅-C₇         cycloalkenyl, each optionally substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and         S(O)_(m)R^(9a);     -   each R^(6a) is independently H, C₁-C₆ alkyl, C(O)R¹³ or         C(O)OR¹³;     -   each R⁷ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₅-C₇         cycloalkenyl, each optionally substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and         S(O)_(m)R^(9a); or phenyl optionally substituted with 1 to 3         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄         alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C(X)R^(7a),         C(O)OR^(8a), C(O)NR¹¹R¹², OR^(4a), C₂-C₆ alkoxyalkyl,         S(O)_(m)R^(9a), S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and         N(R¹⁰)C(O)R^(7a);     -   each R^(7a) is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl;     -   each R⁸ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₅-C₇         cycloalkenyl, each optionally substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and         S(O)_(m)R^(9a); or C₁-C₆ alkyl substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆ alkyl, C₁-C₆ haloalkyl,         C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆         haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ and         S(O)₂NR¹¹R¹²; or phenyl optionally substituted with 1 to 3         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄         alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C(X)R^(7a),         C(O)OR^(8a), C(O)NR¹¹R¹², OR^(4a), C₂-C₆ alkoxyalkyl,         S(O)_(m)R^(9a), S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and         N(R¹⁰)C(O)R^(7a);     -   each R^(8a) is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl;     -   each R⁹ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₁-C₆ alkyl substituted with 1 to 4 substituents         independently selected from the group consisting of halogen,         cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl,         C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²; or         phenyl optionally substituted with 1 to 3 substituents         independently selected from the group consisting of halogen,         cyano, nitro, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄         haloalkyl, C₂-C₄ haloalkenyl, C(X)R^(7a), C(O)OR^(8a),         C(O)NR¹¹R¹², OR^(4a), C₂-C₆ alkoxyalkyl, S(O)_(m)R^(9a),         S(O)₂NR¹¹R¹², NR^(5a)R^(6a), OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);     -   each R^(9a) is independently C₁-C₆ alkyl or C₁-C₆ haloalkyl;     -   each R¹⁰ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl,         C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) or         S(O)₂NR¹¹R¹²;     -   each R^(10a) is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl,         C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆         haloalkynyl;     -   each R¹¹ is independently H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆         alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl;         or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₅-C₇         cycloalkenyl, each optionally substituted with 1 to 4         substituents independently selected from the group consisting of         halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and         S(O)_(m)R^(9a); or C₁-C₆ alkyl substituted with halogen, cyano,         nitro, OR^(4a), NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆ haloalkyl,         C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆         haloalkynyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR^(11a)R¹²,         S(O)_(m)R^(9a) or S(O)₂NR^(11a)R¹²; or phenyl optionally         substituted with 1 to 3 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄         haloalkenyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR^(11a)R¹², OR^(4a),         C₂-C₆ alkoxyalkyl, S(O)_(m)R^(9a), S(O)₂NR^(11a)R¹²,         NR^(5a)R^(6a), OC(O)R^(7a) and N(R^(10a))C(O)R^(7a);     -   each R^(11a) is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl or         C₂-C₆ alkynyl;     -   each R¹² is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl or C₂-C₆         alkynyl;     -   each R¹³ is independently H or C₁-C₄ alkyl;     -   each R¹⁴ is independently C₃-C₇ cycloalkyl, C₄-C₈         cycloalkylalkyl or C₅-C₇ cycloalkenyl, each optionally         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl,         C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or C₁-C₆ alkyl         substituted with 1 to 4 substituents independently selected from         the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆         alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆         alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹ and S(O)₂NR¹¹R¹²; or phenyl, naphthalenyl or a 5- or         6-membered heteroaromatic ring, each optionally substituted with         1 to 5 substituents independently selected from the group         consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl,         C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄         haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a);     -   each m is independently 0, 1 or 2; and     -   n is 0, 1, 2, 3 or 4.

Embodiment 16

A compound of Formula 1p wherein Z is O.

Embodiment 17

A compound of Formula 1p wherein Z is S.

Embodiment 18

A compound of Formula 1p or Embodiment 1 or 2 wherein each R¹ is independently halogen, cyano, nitro, OR⁴, C₁-C₆ alkyl or C₁-C₆ haloalkyl.

Embodiment 18a

A compound of Embodiment 18 wherein each R¹ is independently halogen, C₁-C₆ haloalkyl or C₁-C₆ haloalkoxy (i.e. OR⁴ and R⁴ is C₁-C₆ haloalkyl).

Embodiment 18b

A compound of Embodiment 18a wherein n is 2, and one R¹ is in the 3-position, and a second R¹ is in the 5-position.

Embodiment 18c

A compound of Embodiment 18a or 18b wherein each R¹ is independently halogen or C₁-C₂ haloalkyl.

Embodiment 18d

A compound of Embodiment 18c wherein each R¹ is independently Cl, Br or CF₃.

Embodiment 18e

A compound of Embodiment 18c wherein n is 2, and each R¹ is independently Cl, Br or CF₃.

Embodiment 18f

A compound of Formula 1p wherein n is 1, and R¹ is CF₃ and is in the 3-position.

Embodiment 18g

A compound of Formula 1p wherein n is 2, and one R¹ is CF₃ and is in the 3-position, and a second R¹ is Cl and is in the 5-position.

Embodiment 18h

A compound of Formula 1p wherein n is 2, and one R¹ is CF₃ and is in the 3-position, and a second R¹ is Br and is in the 5-position.

Embodiment 19

A compound of Formula 1p or any of Embodiments 15-18h wherein Q is phenyl or a 5- or 6-membered heteroaromatic ring, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 19a

A compound of Embodiment 19 wherein Q is phenyl, pyridinyl, pyrazolyl, oxazolyl, thiazolyl, isoxazolyl, isothiazolyl or thienyl, each optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 19b

A compound of Embodiment 19a wherein Q is phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 19c

A compound of Embodiment 19a wherein Q is pyridinyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a)

Embodiment 19d

A compound of Embodiment 19a wherein Q is pyrazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 19e

A compound of Embodiment 19a wherein Q is oxazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 19f

A compound of Embodiment 19a wherein Q is thiazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 19g

A compound of Embodiment 19a wherein Q is isoxazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 19h

A compound of Embodiment 19a wherein Q is isothiazolyl optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 19i

A compound of Embodiment 19a wherein Q is thienyl optionally substituted with 1 to 3 substituents independently selected from the group

consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment 19j

A compound of Embodiment 19b wherein Q is phenyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, OR⁴, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C(X)R⁷ and C(O)OR⁸.

Embodiment 19k

A compound of Embodiment 19c wherein Q is pyridinyl optionally substituted with 1 to 3 substituents independently selected from the group consisting of halogen, cyano, OR⁴, C₁-C₄ alkyl, C₁-C₄ haloalkyl, C(X)R⁷ and C(O)OR⁸.

Embodiment 20

A compound of Formula 1p or any of Embodiments 15-19k wherein

R² is H, halogen or C₁-C₆ alkyl.

Embodiment 20a

A compound of Embodiment 20 wherein R² is H, F, Cl, Br or C₁-C₂ alkyl.

Embodiment 20b

A compound of Embodiment 20a wherein R² is H, Cl, Br or CH₃.

Embodiment 21

A compound of Formula 1p or any of Embodiments 15-20b wherein R³ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C(X)R⁷, C(O)OR⁸ or S(O)_(m)R⁹; or C₁-C₆ alkyl substituted with 1 or 20R⁴.

Embodiment 21a

A compound of Embodiment 21 wherein R³ is H or C₁-C₆ alkyl.

Embodiment 21b

A compound of Embodiment 21a wherein R³ is H.

Embodiment 22

A compound of Formula 1p or any of Embodiments 15-21b wherein

R⁴ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl; or C₁-C₆ alkyl substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, OR^(4a), NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) or S(O)₂NR¹¹R¹².

Embodiment 23

A compound of Formula 1p or any of Embodiments 15-22 wherein R⁵ is H, NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹²; or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

Embodiment 24

A compound of Formula 1p or any of Embodiments 15-23 wherein R⁶ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl or C₂-C₆ alkynyl; or C₃-C₇ cycloalkyl or C₄-C₈ cycloalkylalkyl, each optionally substituted with 1 or 2 substituents independently selected from the group consisting of halogen, cyano, C₁-C₄ alkyl, C₁-C₄ haloalkyl and OR^(4a);

Embodiment 25

A compound of Formula 1p or any of Embodiments 15-24 wherein R⁷ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl; or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a).

Embodiment 26

A compound of Formula 1p or any of Embodiments 15-25 wherein R⁸ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl; or C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or C₁-C₆ alkyl substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, OR^(4a), NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) or S(O)₂NR¹¹R¹².

Embodiment 27

A compound of Formula 1p or any of Embodiments 15-26 wherein R⁹ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl or C₂-C₆ haloalkynyl; or C₁-C₆ alkyl substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, OR^(4a), NR^(5a)R^(6a), C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R^(7a), C(O)OR^(8a), C(O)NR¹¹R¹², S(O)_(m)R^(9a) or S(O)₂NR¹¹R¹².

Embodiment 28

A compound of Formula 1p or any of Embodiments 15-27 wherein R¹⁰ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl or C₂-C₆ alkynyl.

Embodiment 29

A compound of Formula 1p or any of Embodiments 15-28 wherein R¹⁴ is C₃-C₇ cycloalkyl, C₄-C₈ cycloalkylalkyl or C₅-C₇ cycloalkenyl, each optionally substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, C₁-C₄ alkyl, C₁-C₄ haloalkyl, OR^(4a) and S(O)_(m)R^(9a); or C₁-C₆ alkyl substituted with 1 to 4 substituents independently selected from the group consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C₂-C₆ alkenyl, C₂-C₆ haloalkenyl, C₂-C₆ alkynyl, C₂-C₆ haloalkynyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹ or S(O)₂NR¹¹R¹².

Embodiments of this invention, including Embodiments 15-29 above as well as any other embodiments described herein, can be combined in any manner, and the descriptions of variables in the embodiments pertain not only to the compounds of Formula 1p but also to the starting compounds and intermediate compounds useful for preparing the compounds of Formula 1p. In addition, embodiments of this invention, including Embodiments 15-29 above as well as any other embodiments described herein, and any combination thereof, pertain to the compositions and methods of the present invention.

Combinations of Embodiments 14-29 are illustrated by:

Embodiment A1

A compound of Formula 1p wherein

-   -   Z is O; and     -   Q is phenyl or a 5- or 6-membered heteroaromatic ring, each         optionally substituted with 1 to 3 substituents independently         selected from the group consisting of halogen, cyano, nitro,         OR⁴, NR⁵R⁶, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄         haloalkyl, C₂-C₄ haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷,         C(O)OR⁸, C(O)NR¹¹R¹², S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and         N(R¹⁰)C(O)R^(7a).

Embodiment B1

A compound of Embodiment A1 wherein

-   -   Q is phenyl, pyridinyl, pyrazolyl, oxazolyl, thiazolyl,         isoxazolyl, isothiazolyl or thienyl, each optionally substituted         with 1 to 3 substituents independently selected from the group         consisting of halogen, cyano, nitro, OR⁴, NR⁵R⁶, C₁-C₄ alkyl,         C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₁-C₄ haloalkyl, C₂-C₄         haloalkenyl, C₂-C₆ alkoxyalkyl, C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹²,         S(O)_(m)R⁹, S(O)₂NR¹¹R¹², OC(O)R^(7a) and N(R¹⁰)C(O)R^(7a).

Embodiment C1

A compound of Embodiment B1 wherein

-   -   each R¹ is independently H, halogen, cyano, nitro, OR⁴, C₁-C₆         alkyl or C₁-C₆ haloalkyl;     -   R² is H, halogen or C₁-C₆ alkyl;     -   R³ is H, C₁-C₆ alkyl, C₁-C₆ haloalkyl, C(X)R⁷, C(O)OR⁸ or         S(O)_(m)R⁹; or C₁-C₆ alkyl substituted with 1 or 20R⁴; and     -   n is 1 or 2.

Of note is that compounds of this invention are characterized by favorable metabolic and/or soil residual patterns and exhibit activity controlling a spectrum of agronomic and nonagronomic parasitic nematodes.

Of particular note, for reasons of parasitic nematode control spectrum and economic importance, protection of agronomic crops from damage or injury caused by parasitic nematodes by controlling parasitic nematodes are embodiments of the invention. Compounds of this invention because of their favorable translocation properties or systemicity in plants also protect foliar or other plant parts which are not directly contacted with a compound of Formula 1 or a composition comprising the compound.

Also noteworthy as embodiments of the present invention are compositions comprising a compound of any of the preceding Embodiments, as well as any other embodiments described herein, and any combinations thereof, and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, said compositions optionally further comprising at least one additional biologically active compound or agent.

Further noteworthy as embodiments of the present invention are compositions for controlling a parasitic nematode comprising a compound of any of the preceding Embodiments, as well as any other embodiments described herein, and any combinations thereof, and at least one additional component selected from the group consisting of a surfactant, a solid diluent and a liquid diluent, said compositions optionally further comprising at least one additional biologically active compound or agent. Embodiments of the invention further include methods for controlling a parasitic nematode comprising contacting the parasitic nematode or its environment with a biologically effective amount of a compound of any of the preceding Embodiments (e.g., as a composition described herein).

Embodiments of the invention also include a composition comprising a compound of any of the preceding Embodiments, in the form of a soil drench liquid formulation. Embodiments of the invention further include methods for controlling a parasitic nematode comprising contacting the soil with a liquid composition as a soil drench comprising a biologically effective amount of a compound of any of the preceding Embodiments.

Embodiments of the invention also include a spray composition for controlling a parasitic nematode comprising a biologically effective amount of a compound of any of the preceding Embodiments and a propellant. Embodiments of the invention further include a bait composition for controlling a parasitic nematode comprising a biologically effective amount of a compound of any of the preceding Embodiments, one or more food materials, optionally an attractant, and optionally a humectant.

Embodiments of the invention also include methods for protecting a seed from a parasitic nematode comprising contacting the seed with a biologically effective amount of a compound of any of the preceding Embodiments.

Embodiments of the invention also include methods for controlling a parasitic nematode comprising contacting the parasitic nematode or its environment with a biologically effective amount of a compound of Formula 1, an N-oxide, or a salt thereof, (e.g., as a composition described herein), provided that the methods are not methods of medical treatment of a human or animal body by therapy.

This invention also relates to such methods wherein the parasitic nematode or its environment is contacted with a composition comprising a biologically effective amount of a compound of Formula 1, an N-oxide, or a salt thereof, and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, said composition optionally further comprising a biologically effective amount of at least one additional biologically active compound or agent, provided that the methods are not methods of medical treatment of a human or animal body by therapy.

One or more of the following methods and variations as described in Schemes 1-8 can be used to prepare the compounds of Formula 1. The definitions of X, Q, R¹, R² and R³ in the compounds of Formulae 1a-1c and 2-10 below are as defined above in the Summary of the Invention unless otherwise noted. Formulae 1a-1c are various subsets of Formula 1, and all substituents for Formulae 1a-1c are as defined above for Formula 1 unless otherwise noted. Room temperature is between about 20 and 25° C.

Compounds of Formula 1a (i.e. Formula 1 wherein Z is oxygen and R³ is H) can be prepared by the reaction of carboxylic acids of Formula 2 with aryl or heteroaryl sulfonamides of Formula 3 as shown in Scheme 1. Typically, an amide coupling reagent and a catalyst such as N,N-dimethylaminopyridine (DMAP) are used in the method of Scheme 1. Amide coupling reagents include 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (EDC), N,N′-dicyclohexylcarbodiimide (DCC) and 1,1′-carbonyldiimidazole (CDI). The reaction can be carried out at temperatures ranging from room temperature to the reflux temperature of the solvent. Typical solvents include alcohols, ethers, esters, amides and halogenated hydrocarbons. Step D of Synthesis Example 1 describes a particularly useful set of conditions utilizing EDC/DMAP in a 1:1 solvent mixture of t-butanol and dichloromethane.

Compounds of Formula 1a can also be prepared by the reaction of carboxylic acid chlorides of Formula 4 with aryl or heteroaryl sulfonamides of Formula 3 as shown in Scheme 2. The reaction typically involves use of a base such as triethylamine or pyridine and optionally a catalyst such as DMAP in the presence of a solvent. The reaction can be carried out at temperatures ranging from room temperature to the reflux temperature of the solvent. Typical solvents include ethers, esters and halogenated hydrocarbons.

Compounds of Formula 1b wherein R³ is optionally substituted alkyl, alkenyl, alkynyl or cycloalkyl can be prepared by the reaction of compounds of Formula 1a with appropriately substituted alkyl, alkenyl, alkynyl or cycloalkyl halides and base as shown in Scheme 3. Typical reaction conditions comprise potassium carbonate as the base and DMF as the solvent.

Compounds of Formula 1b wherein R³ is C(X)R⁷, C(O)OR⁸, C(O)NR¹¹R¹², S(O)₂R⁹ or S(O)₂NR¹¹R¹² can be prepared by the reaction of compounds of Formula 1a with acyl or sulfonyl halides (e.g., ClC(X)R⁷, ClC(O)OR⁸, ClC(O)NR¹¹R¹², ClS(O)₂R⁹ or ClS(O)₂NR¹¹R¹²) by acylation or sulfonylation methods well known in the art.

Compounds of Formula 1b wherein R³ is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or phenyl can be prepared by the reaction of acid chlorides of Formula 4 with sulfonamides of Formula 9 as shown in Scheme 4. Alternatively, compounds of Formula 1b wherein R³ is optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or phenyl can be prepared by the reaction of carboxylic acids of Formula 2 with sulfonamides of Formula 9 by the method of Scheme 1.

Thioamides of Formula 1c (i.e. Formula 1 wherein X is sulfur) can be prepared by the reaction of compounds of Formula 1b (i.e. Formula 1 wherein X is O) with thiation reagents such as phosphorus pentasulfide or Lawesson's reagent as depicted in Scheme 5.

Compounds of Formula 2b (i.e. Formula 2 wherein R² is bromine) can be prepared by the reaction of compounds of Formula 2a (i.e. Formula 2 wherein R² is H) with bromine in acetic acid in the presence of sodium acetate as described in Heterocycles 2002, 57(1), 21-38.

Compounds of Formula 2 wherein R² is cyano can be prepared by reaction of compounds of Formula 2b with CuCN by methods known in the art. Compounds of Formula 2 wherein R² is nitro can be prepared by reaction of compounds of Formula 2a with nitric acid/sulfuric acid as described in Bioorganic Med. Chem. Lett. 2005, 15(11), 2790-2794. Compounds of Formula 2 wherein R² is OR⁴, NR⁵R⁶ or SR⁹ can be prepared from compounds of Formula 2 wherein R² is F by standard displacement reactions well known in the art. Compounds of Formula 2 wherein R² is F can be prepared as described in Russian Chem. Bull. 2005, 54(2), 470-471.

Carboxylic acids of Formula 2 and acid chlorides of Formula 4 can be prepared by the reactions shown in Scheme 7. Reaction of a suitably substituted 2-aminopyridine of Formula 5 with a 2-bromopyruvate of Formula 6 wherein R² is H, optionally substituted alkyl, alkenyl, alkynyl, C(O)R⁷, C(O)OR⁸ or C(O)NR¹¹R¹², or an optionally substituted phenyl, naphthalenyl or a 5- or 6-membered heteroaromatic ring at temperatures ranging from room temperature to the boiling temperature of the solvent affords the carboxylic ester of Formula 7 along with variable amounts of the alcohol of Formula 8. Heating the reaction mixture to boiling in a solvent such as 1,2-dimethoxyethane results in complete conversion of alcohol 8 to ester 7. Treatment of a mixture of esters 7 and 8 with an aqueous hydroxide base such as sodium hydroxide in a water-miscible solvent such as ethanol results in ester hydrolysis to form the carboxylic acid of Formula 2 after acidification with a strong acid such as hydrochloric acid. This method is detailed in Step C of Synthesis Example 1. The carboxylic acid of Formula 2 can be converted to the acid chloride of Formula 4 by well known conventional means such as treatment with thionyl chloride or oxalyl chloride with a catalytic amount of N,N-dimethylformamide (DMF) in moderately polar, aprotic solvents including dichloromethane, dichloroethane, toluene and ethyl acetate. Intermediates of Formula 6 can be prepared by a variety of well-known synthetic methods, including the bromination of optionally substituted pyruvates or lactates (alpha-hydroxy esters). Typical reaction conditions include direct bromination with bromine (see, for example, JACS 1944, 66, 1656-1659) or CuBr₂ in ethyl acetate/chloroform (see, for example, JOC 2002, 67(4), 1102-1108), or reaction of a lactate with N-bromosuccinimide in CCl₄ (see, for example, JACS 1954, 76, 5796-5797).

Sulfonamides of Formulae 3 and 9 are known in the chemical literature or are available commercially. As shown in Scheme 8, sulfonamides of Formula 3 are readily prepared from the corresponding sulfonyl chlorides of Formula 10 by reaction with ammonia, while sulfonamides of Formula 9 are readily prepared from the corresponding sulfonyl chlorides of Formula 10 by reaction with R³NH₂. The sulfonyl chloride intermediates are available commercially or can be prepared by a large variety of methods known in the literature. Three of the most common methods of sulfonyl chloride preparation are shown in Scheme 8, including (a) direct chlorosulfonylation of aromatic and heteroaromatic systems with chlorosulfonic acid, (b) oxidation of sulfides (for example with sodium hypochlorite) in the presence of hydrochloric acid, and (c) diazotization and chlorosulfonylation of aromatic and heteroaromatic amines. These three methods are meant only to be illustrative; a large variety of other synthetic methods are available for the preparation of sulfonyl chlorides and sulfonamides.

Examples of intermediates useful in the preparation of compounds of this invention are shown in Tables I-1 through I-12. The following abbreviations are used in the Tables which follow: Me means methyl, Et means ethyl, i-Pr means isopropyl, n-Pr means normal propyl, OMe means methoxy and SMe means thiomethoxy.

TABLE I-1

R^(1a) R^(1b) R² R^(x) H H H Cl H H H OH H H H OCH₃ H H H OCH₂CH₃ CF₃ H H Cl CF₃ H H OH CF₃ H H OCH₃ CF₃ H H OCH₂CH₃ CF₃ Cl H Cl CF₃ Cl H OH CF₃ Cl H OCH₃ CF₃ Cl H OCH₂CH₃ CF₃ Br H Cl CF₃ Br H OH CF₃ Br H OCH₃ CF₃ Br H OCH₂CH₃ Cl H H Cl Cl H H OH Cl H H OCH₃ Cl H H OCH₂CH₃ Cl Cl H Cl Cl Cl H OH Cl Cl H OCH₃ Cl Cl H OCH₂CH₃ Br H H Cl Br H H OH Br H H OCH₃ Br H H OCH₂CH₃ Br Br H Cl Br Br H OH Br Br H OCH₃ Br Br H OCH₂CH₃ H H Br Cl H H Br OH H H Br OCH₃ H H Br OCH₂CH₃ CF₃ H Br Cl CF₃ H Br OH CF₃ H Br OCH₃ CF₃ H Br OCH₂CH₃ CF₃ Cl Br Cl CF₃ Cl Br OH CF₃ Cl Br OCH₃ CF₃ Cl Br OCH₂CH₃ CF₃ Br Br Cl CF₃ Br Br OH CF₃ Br Br OCH₃ CF₃ Br Br OCH₂CH₃ Cl H Br Cl Cl H Br OH Cl H Br OCH₃ Cl H Br OCH₂CH₃ Cl Cl Br Cl Cl Cl Br OH Cl Cl Br OCH₃ Cl Cl Br OCH₂CH₃ Br H Br Cl Br H Br OH Br H Br OCH₃ Br H Br OCH₂CH₃ Br Br Br Cl Br Br Br OH Br Br Br OCH₃ Br Br Br OCH₂CH₃ H H Cl Cl H H Cl OH H H Cl OCH₃ H H Cl OCH₂CH₃ CF₃ H Cl Cl CF₃ H Cl OH CF₃ H Cl OCH₃ CF₃ H Cl OCH₂CH₃ CF₃ Cl Cl Cl CF₃ Cl Cl OH CF₃ Cl Cl OCH₃ CF₃ Cl Cl OCH₂CH₃ CF₃ Br Cl Cl CF₃ Br Cl OH CF₃ Br Cl OCH₃ CF₃ Br Cl OCH₂CH₃ Cl H Cl Cl Cl H Cl OH Cl H Cl OCH₃ Cl H Cl OCH₂CH₃ Cl Cl Cl Cl Cl Cl Cl OH Cl Cl Cl OCH₃ Cl Cl Cl OCH₂CH₃ Br H Cl Cl Br H Cl OH Br H Cl OCH₃ Br H Cl OCH₂CH₃ Br Br Cl Cl Br Br Cl OH Br Br Cl OCH₃ Br Br Cl OCH₂CH₃ H H CH₃ Cl H H CH₃ OH H H CH₃ OCH₃ H H CH₃ OCH₂CH₃ CF₃ H CH₃ Cl CF₃ H CH₃ OH CF₃ H CH₃ OCH₃ CF₃ H CH₃ OCH₂CH₃ CF₃ Cl CH₃ Cl CF₃ Cl CH₃ OH CF₃ Cl CH₃ OCH₃ CF₃ Cl CH₃ OCH₂CH₃ CF₃ Br CH₃ Cl CF₃ Br CH₃ OH CF₃ Br CH₃ OCH₃ CF₃ Br CH₃ OCH₂CH₃ Cl H CH₃ Cl Cl H CH₃ OH Cl H CH₃ OCH₃ Cl H CH₃ OCH₂CH₃ Cl Cl CH₃ Cl Cl Cl CH₃ OH Cl Cl CH₃ OCH₃ Cl Cl CH₃ OCH₂CH₃ Br H CH₃ Cl Br H CH₃ OH Br H CH₃ OCH₃ Br H CH₃ OCH₂CH₃ Br Br CH₃ Cl Br Br CH₃ OH Br Br CH₃ OCH₃ Br Br CH₃ OCH₂CH₃

TABLE I-2

R^(a) R^(b) R^(c) R^(d) R^(e) H H H H H H Me H H H H F H H H H Cl H H H H Br H H H H CF₃ H H H H cyano H H H H OMe H H H H SMe H H H F H H H H F Me H H H F F H H H F Cl H H H F Br H H H F CF₃ H H H F cyano H H H F OMe H H H F SMe H H H Br H H H H Br Me H H H Br F H H H Br Cl H H H Br Br H H H Br CF₃ H H H Br cyano H H H Br OMe H H H Br SMe H H H cyano H H H H cyano Me H H H cyano F H H H cyano Cl H H H Me H H H H Me Me H H H Me F H H H Me Cl H H H Me Br H H H Me CF₃ H H H Me cyano H H H Me OMe H H H Me SMe H H H Cl H H H H Cl Me H H H Cl F H H H Cl Cl H H H Cl Br H H H Cl CF₃ H H H Cl cyano H H H Cl OMe H H H Cl SMe H H H CF₃ H H H H CF₃ Me H H H CF₃ F H H H CF₃ Cl H H H CF₃ Br H H H CF₃ CF₃ H H H CF₃ cyano H H H CF₃ OMe H H H CF₃ SMe H H H cyano Br H H H cyano CF₃ H H H cyano cyano H H H cyano OMe H H H cyano SMe H H H

TABLE I-2a

R^(a) R^(b) R^(c) R^(d) R^(e) H H H H H H H H Me H H H H Et H H H H i-Pr H H H H F H H H H Cl H H H H Br H H H H CF₃ H H H H cyano H H H H OMe H H H H OEt H H H H OCH(CH₃)₂ H H H H OCH₂CF₃ H H H H SMe H H H H C(O)CH₃ H F H H H H F H H Me H F H H Et H F H H i-Pr H F H H F H F H H Cl H F H H Br H F H H CF₃ H F H H cyano H F H H OMe H F H H OEt H F H H OCH(CH₃)₂ H F H H OCH₂CF₃ H F H H SMe H F H H C(O)CH₃ H Br H H H H Br H H Me H Br H H Et H Br H H i-Pr H Br H H F H Br H H Cl H Br H H Br H Br H H CF₃ H Br H H cyano H Br H H OMe H Br H H OEt H Br H H OCH(CH₃)₂ H Br H H OCH₂CF₃ H Br H H SMe H Br H H C(O)CH₃ H cyano H H H H cyano H H Me H cyano H H Et H cyano H H i-Pr H cyano H H F H cyano H H Cl H cyano H H Br H Me H H H H Me H H Me H Me H H Et H Me H H i-Pr H Me H H F H Me H H Cl H Me H H Br H Me H H CF₃ H Me H H cyano H Me H H OMe H Me H H OEt H Me H H OCH(CH₃)₂ H Me H H OCH₂CF₃ H Me H H SMe H Me H H C(O)CH₃ H Cl H H H H Cl H H Me H Cl H H Et H Cl H H i-Pr H Cl H H F H Cl H H Cl H Cl H H Br H Cl H H CF₃ H Cl H H cyano H Cl H H OMe H Cl H H OEt H Cl H H OCH(CH₃)₂ H Cl H H OCH₂CF₃ H Cl H H SMe H Cl H H C(O)CH₃ H CF₃ H H H H CF₃ H H Me H CF₃ H H Et H CF₃ H H i-Pr H CF₃ H H F H CF₃ H H Cl H CF₃ H H Br H CF₃ H H CF₃ H CF₃ H H cyano H CF₃ H H OMe H CF₃ H H OEt H CF₃ H H OCH(CH₃)₂ H CF₃ H H OCH₂CF₃ H CF₃ H H SMe H CF₃ H H C(O)CH₃ H cyano H H CF₃ H cyano H H cyano H cyano H H OMe H cyano H H OEt H cyano H H OCH(CH₃)₂ H cyano H H OCH₂CF₃ H cyano H H SMe H cyano H H C(O)CH₃ H

TABLE I-2b

R^(a) R^(b) R^(c) R^(d) R^(e) H H F H H H H F Cl H H H F Br H H H F Me H H H F Et H H H F OMe H H H F acetyl H H H Cl H H H H Cl Cl H H H Cl Br H H H Cl Me H H H Cl Et H H H Cl OMe H H H Cl acetyl H H H Br H H H H Br Cl H H H Br Br H H H Br Me H H H Br Et H H H Br OMe H H H Br acetyl H H H Me H H H H Me Cl H H H Me Br H H H Me Me H H H Me Et H H H Me OMe H H H Me acetyl H Br H F H H Br H F Cl H Br H F Br H Br H F Me H Br H F Et H Br H F OMe H Br H F acetyl H Br H Cl H H Br H Cl Cl H Br H Cl Br H Br H Cl Me H Br H Cl Et H Br H Cl OMe H Br H Cl acetyl H Br H Br H H Br H Br Cl H Br H Br Br H Br H Br Me H Br H Br Et H Br H Br OMe H Br H Br acetyl H Br H Me H H Br H Me Cl H Br H Me Br H Br H Me Me H Br H Me Et H Br H Me OMe H Br H Me acetyl H Cl H F H H Cl H F Cl H Cl H F Br H Cl H F Me H Cl H F Et H Cl H F OMe H Cl H F acetyl H Cl H Cl H H Cl H Cl Cl H Cl H Cl Br H Cl H Cl Me H Cl H Cl Et H Cl H Cl OMe H Cl H Cl acetyl H Cl H Br H H Cl H Br Cl H Cl H Br Br H Cl H Br Me H Cl H Br Et H Cl H Br OMe H Cl H Br acetyl H Cl H Me H H Cl H Me Cl H Cl H Me Br H Cl H Me Me H Cl H Me Et H Cl H Me OMe H Cl H Me acetyl H Me H F H H Me H F Cl H Me H F Br H Me H F Me H Me H F Et H Me H F OMe H Me H F acetyl H Me H Cl H H Me H Cl Cl H Me H Cl Br H Me H Cl Me H Me H Cl Et H Me H Cl OMe H Me H Cl acetyl H Me H Br H H Me H Br Cl H Me H Br Br H Me H Br Me H Me H Br Et H Me H Br OMe H Me H Br acetyl H Me H Me H H Me H Me Cl H Me H Me Br H Me H Me Me H Me H Me Et H Me H Me OMe H Me H Me acetyl H

TABLE I-3

R^(a) R^(b) R^(c) H H H H H Me H H Cl H H Br H Me H H Me Me H Me Cl H Me Br H Et H H Et Me H Et Cl H Et Br H Cl H H Cl Me H Cl Cl H Cl Br Br H H Br H Me Br H Cl Br H Br Br Me H Br Me Me Br Me Cl Br Me Br Br Et H Br Et Me Br Et Cl Br Et Br Br Cl H Br Cl Me Br Cl Cl Br Cl Br Me H H Me H Me Me H Cl Me H Br Me Me H Me Me Me Me Me Cl Me Me Br Me Et H Me Et Me Me Et Cl Me Et Br Me Cl H Me Cl Me Me Cl Cl Me Cl Br Et H H Et H Me Et H Cl Et H Br Et Me H Et Me Me Et Me Cl Et Me Br Et Et H Et Et Me Et Et Cl Et Et Br Et Cl H Et Cl Me Et Cl Cl Et Cl Br Cl H H Cl H Me Cl H Cl Cl H Br Cl Me H Cl Me Me Cl Me Cl Cl Me Br Cl Et H Cl Et Me Cl Et Cl Cl Et Br Cl Cl H Cl Cl Me Cl Cl Cl Cl Cl Br

TABLE I-4

R^(a) R^(b) R^(c) H H H H H Me H H Cl H Me H H Me Me H Me Cl H Et H H Et Me H Et Cl Et H H Et H Me Et H Cl Et Me H Et Me Me Et Me Cl Et Et H Et Et Me Et Et Cl Me H H Me H Me Me H Cl Me Me H Me Me Me Me Me Cl Me Et H Me Et Me Me Et Cl Br H H Br H Me Br H Cl Br Me H Br Me Me Br Me Cl Br Et H Br Et Me Br Et Cl Cl H H Cl H Me Cl H Cl Cl Me H Cl Me Me Cl Me Cl Cl Et H Cl Et Me Cl Et Cl

TABLE I-5

R^(a) R^(b) H H H Me H Cl Me H Me Me Me Cl Cl H Cl Me Cl Cl

TABLE I-6

R^(a) R^(b) H H H Me H Cl Me H Me Me Me Cl Cl H Cl Me Cl Cl

TABLE I-7

R^(a) R^(b) R^(c) H H Me H H Et H H i-Pr H H n-Pr Br H Me Br H Et Br H i-Pr Br H n-Pr Cl Me Me Cl Me Et Cl Me i-Pr Cl Me n-Pr Me Cl Me Me Cl Et Me Cl i-Pr Me Cl n-Pr H Br Me H Br Et H Br i-Pr H Br n-Pr Br Br Me Br Br Et Br Br i-Pr Br Br n-Pr Me H Me Me H Et Me H i-Pr Me H n-Pr H Me Me H Me Et H Me i-Pr H Me n-Pr Br Me Me Br Me Et Br Me i-Pr Br Me n-Pr Cl Cl Me Cl Cl Et Cl Cl i-Pr Cl Cl n-Pr Me Br Me Me Br Et Me Br i-Pr Me Br n-Pr Cl H Me Cl H Et Cl H i-Pr Cl H n-Pr Me Me Me Me Me Et Me Me i-Pr Me Me n-Pr H Cl Me H Cl Et H Cl i-Pr H Cl n-Pr Br Cl Me Br Cl Et Br Cl i-Pr Br Cl n-Pr Cl Br Me Cl Br Et Cl Br i-Pr Cl Br n-Pr

TABLE I-8

R^(a) R^(b) H H H Cl H Me H Et H i-Pr H n-Pr Me H Me Cl Me Me Me Et Me i-Pr Me n-Pr Cl H Cl Cl Cl Me Cl Et Cl i-Pr Cl n-Pr Br H Br Cl Br Me Br Et Br i-Pr Br n-Pr

TABLE I-9

R^(a) R^(b) R^(c) H H Me H H Et H H i-Pr H H n-Pr Br H Me Br H Et Br H i-Pr Br H n-Pr Cl Me Me Cl Me Et Cl Me i-Pr Cl Me n-Pr Me Cl Me Me Cl Et Me Cl i-Pr Me Cl n-Pr H Br Me H Br Et H Br i-Pr H Br n-Pr Br Br Me Br Br Et Br Br i-Pr Br Br n-Pr Me H Me Me H Et Me H i-Pr Me H n-Pr H Me Me H Me Et H Me i-Pr H Me n-Pr Br Me Me Br Me Et Br Me i-Pr Br Me n-Pr Cl Cl Me Cl Cl Et Cl Cl i-Pr Cl Cl n-Pr Me Br Me Me Br Et Me Br i-Pr Me Br n-Pr Cl H Me Cl H Et Cl H i-Pr Cl H n-Pr Me Me Me Me Me Et Me Me i-Pr Me Me n-Pr H Cl Me H Cl Et H Cl i-Pr H Cl n-Pr Br Cl Me Br Cl Et Br Cl i-Pr Br Cl n-Pr Cl Br Me Cl Br Et Cl Br i-Pr Cl Br n-Pr

TABLE I-10

R^(a) R^(b) R^(c) R^(d) Me H H H Me H H Me Me H H OMe Me OMe H H Me OMe H Me Me OMe H OMe Me H Me H Me H Me Me Me H Me OMe Me OMe Me H Me OMe Me Me Me OMe Me OMe Me Me H H Me Me H Me Me Me H OMe Me Me Me H Me Me Me Me Me Me Me OMe Br H H H Br H H Me Br H H OMe Br OMe H H Br OMe H Me Br OMe H OMe Br H Me H Br H Me Me Br H Me OMe Cl H H H Cl H H Me Cl H H OMe Cl OMe H H Cl OMe H Me Cl OMe H OMe Cl H Me H Cl H Me Me Cl H Me OMe Cl OMe Me H Cl OMe Me Me Cl OMe Me OMe Cl Me H H Cl Me H Me Cl Me H OMe Cl Me Me H Cl Me Me Me Cl Me Me OMe Br OMe Me H Br OMe Me Me Br OMe Me OMe Br Me H H Br Me H Me Br Me H OMe Br Me Me H Br Me Me Me Br Me Me OMe

TABLE I-11

R^(a) R^(b) R^(c) R^(d) H H H H H H H Me H H H CF₃ H H H Cl H H H Br H H Me H H H Me Me H H Me CF₃ H H Me Cl H H Me Br H Cl H H H Cl H Me H Cl H CF₃ H Cl H Cl H Cl H Br H Cl Me H H Cl Me Me H Cl Me CF₃ H Cl Me Cl H Cl Me Br H Me H H H Me H Me H Me H CF₃ H Me H Cl H Me H Br H Me Me H H Me Me Me H Me Me CF₃ H Me Me Cl H Me Me Br H CF₃ H H H CF₃ H Me H CF₃ H CF₃ H CF₃ H Cl H CF₃ H Br H CF₃ Me H H CF₃ Me Me H CF₃ Me CF₃ H CF₃ Me Cl H CF₃ Me Br H OMe H H H OMe H Me H OMe H CF₃ H OMe H Cl H OMe H Br H OMe Me H H OMe Me Me H OMe Me CF₃ H OMe Me Cl H OMe Me Br Me H H H Me H H Me Me H H CF₃ Me H H Cl Me H H Br Me H Me H Me H Me Me Me H Me CF₃ Me H Me Cl Me H Me Br Me Cl H H Me Cl H Me Me Cl H CF₃ Me Cl H Cl Me Cl H Br Me Cl Me H Me Cl Me Me Me Cl Me CF₃ Me Cl Me Cl Me Cl Me Br Me Me H H Me Me H Me Me Me H CF₃ Me Me H Cl Me Me H Br Me Me Me H Me Me Me Me Me Me Me CF₃ Me Me Me Cl Me Me Me Br Me CF₃ H H Me CF₃ H Me Me CF₃ H CF₃ Me CF₃ H Cl Me CF₃ H Br Me CF₃ Me H Me CF₃ Me Me Me CF₃ Me CF₃ Me CF₃ Me Cl Me CF₃ Me Br Me OMe H H Me OMe H Me Me OMe H CF₃ Me OMe H Cl Me OMe H Br Me OMe Me H Me OMe Me Me Me OMe Me CF₃ Me OMe Me Cl Me OMe Me Br

TABLE I-12

R^(a) R^(b) R^(c) R^(d) H H H H H H H Me H H H Cl H H Me H H H Me Me H H Me Cl Me H H H Me H H Me Me H H Cl Me H Me H Me H Me Me Me H Me Cl

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula 1.

One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Synthesis Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Steps in the following Synthesis Examples illustrate a procedure for each step in an overall synthetic transformation, and the starting material for each step may not have necessarily been prepared by a particular preparative run whose procedure is described in other Examples or Steps. ¹H NMR spectra are reported in ppm downfield from tetramethylsilane; “s” means singlet, “d” means doublet, “dd” means doublet of doublets, “br s” means broad singlet. Room temperature is between about 20 and 25° C.

Synthesis Example 1 Preparation of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide Step A: Preparation of 2-chloro-5-methoxybenzenesulfonyl chloride

To a 3-neck flask equipped with a dry ice condenser was added acetic acid (80 mL) and copper chloride (0.8 g). The mixture was cooled to 0° C., sulfur dioxide (5 mL) was condensed into the reaction flask, and then the reaction mixture was stirred for 30 minutes. To a separate 200 mL round-bottom flask was added concentrated hydrochloric acid (32 mL), acetic acid (8 mL) and 2-chloro-5-methylaniline hydrochloride (3.2 g, 16 mmol). This mixture was cooled to 0° C., and sodium nitrite (1.25 g, 18.1 mmol) in water (8 mL) was added dropwise while keeping the temperature below 10° C. The reaction mixture was stirred for 30 minutes and then added dropwise to the sulfur dioxide solution. The resulting reaction mixture was stirred at room temperature for 1 h. Water was added dropwise, and a tan solid precipitated. The solid was isolated by filtration and washed with water to afford 2.5 g the title compound. ¹H NMR (CDCl₃) δ 7.64 (d, 1H), 7.52 (d, 1H), 7.17 (d, 1H), 3.89 (s, 3H).

Step B: Preparation of 2-chloro-5-methoxybenzenesulfonamide

To a solution of 2-chloro-5-methoxybenzenesulfonyl chloride (2.5 g, 10.4 mmol) (i.e. the product of Step A) in tetrahydrofuran (30 mL) was added 30% ammonium hydroxide (3.0 mL, 25.7 mmol) dropwise. The reaction mixture was stirred for 15 minutes, during which time a suspension formed. To this mixture water (10 mL) was added, and the tetrahydrofuran was evaporated under reduced pressure to leave an aqueous suspension of a tan solid. The solid was isolated by filtration and washed with water to afford 2.2 g of the title compound. ¹H NMR (CDCl₃) δ 7.63 (d, 1H), 7.43 (d, 1H), 7.03 (d, 1H), 5.13 (br s, 2H), 3.85 (s, 3H).

Step C: Preparation of 8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid

To a solution of 2-amino-3-chloro-5-(trifluoromethyl)pyridine (24.7 g, 126 mmol) in 1,2-dimethoxyethane (260 mL) at 0° C. was added ethyl bromopyruvate (17.43 mL, 138 mmol) dropwise. The reaction mixture was warmed to room temperature and stirred for three days to form a suspension. The reaction mixture was then extracted with dichloromethane (2×200 mL) and washed with water (2×200 mL). The combined dichloromethane extracts were dried over magnesium sulfate and concentrated under reduced pressure to obtain a solid residue. The combined water washes were saturated with sodium carbonate, extracted with ethyl acetate (2×200 mL), and dried over magnesium sulfate. The combined ethyl acetate extracts and the residue obtained from the concentration of the dichloromethane were combined, and the mixture was concentrated under reduced pressure to obtain a solid.

This solid was dissolved in ethanol (800 mL), and aqueous 50% sodium hydroxide (40 g, 500 mmol) combined with additional water (150 mL) was added dropwise. The reaction mixture was stirred at room temperature overnight to form a suspension. The reaction mixture was acidified to pH 2 with concentrated hydrochloric acid and then cooled and stirred for several hours to precipitate a solid. The solid product was isolated by filtration using a glass-fritted filter funnel, washed with water, and air dried under a stream of air overnight to afford 13 g of the title compound as a solid. ¹H NMR (CDCl₃) δ 8.51 (s, 1H), 8.40 (s, 1H), 7.55 (s, 1H).

Step D: Preparation of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide

To the carboxylic acid from Step C (243 mg, 0.92 mmol) was added a solution of 4-(dimethylamino)pyridine (340 mg, 2.76 mmol) and 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride (232 mg, 2.3 mmol) in t-butanol (5 mL) and dichloromethane (5 mL). The reaction mixture was stirred for 15 min, 2-chloro-5-methoxybenzenesulfonamide (190 mg, 0.86 mmol) was added, and the reaction mixture was stirred at room temperature overnight. Dichloromethane (200 mL) was then added, the mixture was extracted with 1 N hydrochloric acid (3×100 mL), and the separated organic phase was dried over magnesium sulfate and concentrated under reduced pressure to afford a solid. The solid was rinsed with diethyl ether to afford 240 mg of the title compound, a compound of the present invention, as a white solid, m.p. 211-212° C. ¹H NMR (CDCl₃) δ 10.10 (br s, 1H), 8.46 (s, 1H), 8.27 (s, 1H), 7.86 (d, 1H), 7.54 (s, 1H), 7.38 (d, 1H), 7.09 (dd, 1H) 3.91 (s, 3H).

Synthesis Example 2 Preparation of 8-chloro-N-[(4-cyano-2,5-dimethylphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide Step A: Preparation of 4-bromo-2,5-dimethylbenzenesulfonamide

To chlorosulfonic acid (4.2 mL, 63 mmol) cooled to 10° C. was added 2-bromo-p-xylene (5.0 g, 27 mmol) dropwise over 15 min. The reaction mixture was stirred further for 10 min, and then poured with stirring onto 125 mL of crushed ice to precipitate a white solid. The solid was isolated by filtration and washed with water. The solid was dissolved in tetrahydrofuran (40 mL) and an aqueous 30% ammonium hydroxide solution (8.0 mL) was added. The reaction mixture was stirred for 10 min and concentrated under reduced pressure to precipitate a white solid. The solid was isolated by filtration and washed with water to afford 4.6 g of the title compound as a solid. ¹H NMR (CDCl₃) δ 7.87 (s, 1H), 7.52 (s, 1H), 4.75 (br s, 2H), 2.61 (s, 3H), 2.41 (s, 3H).

Step B: Preparation of 4-cyano-2,5-dimethylbenzenesulfonamide

To a solution of 4-bromo-2,5-dimethylbenzenesulfonamide (4.6 g, 22 mmol, the product of Step A) in N-methylpyrrolidinone (30 mL) was added copper cyanide (2.5 g, 28 mmol), and the reaction mixture was heated at 200° C. for 30 min. The reaction was then allowed to cool and poured into 200 mL of crushed ice to precipitate a solid. To this mixture was added dichloromethane (500 mL), and the mixture was warmed to dissolve the white solid. The mixture was then filtered to remove any undissolved solids, the phases were separated, and the dichloromethane was washed with water (2×100 mL), dried over magnesium sulfate, and evaporated under reduced pressure to obtain an oil. The oil was dissolved in tetrahydrofuran (30 mL) and water (30 mL), and the solution was concentrated under reduced pressure to precipitate a solid. This solid was isolated by filtration and washed with water to afford 2.5 g of the title compound. ¹H NMR (CDCl₃) δ 7.98 (s, 1H), 7.56 (s, 1H), 4.89 (br s, 2H), 2.66 (s, 3H), 2.58 (s, 3H).

Step C: Preparation of 8-chloro-N-[(4-cyano-2,5-dimethylphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide

To a solution of 8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid (2.5 g, 9.5 mmol, prepared as described in Example 1 Step C) in t-butanol (70 mL) and dichloromethane (70 mL) was added 4-(dimethylamino)pyridine (3.47 g, 28.4 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (4.54 g, 23.7 mmol). The reaction mixture was stirred for 15 min after which time 4-cyano-2,5-dimethylbenzenesulfonamide (1.85 g, 8.85 mmol) was added, and stirring was continued at room temperature overnight. Dichloromethane (200 mL) was then added, the mixture was washed with 1 N hydrochloric acid (3×100 mL), the organic phase was collected and dried over magnesium sulfate and then concentrated under reduced pressure to afford a solid. The solid was isolated by filtration, rinsed with diethyl ether, and recrystallized from hexane/ethyl acetate to afford 1.5 g of the title compound, a compound of the present invention, as a solid, m.p. 228-229° C. ¹H NMR (CDCl₃) δ 9.97 (br s, 1H), 8.47 (s, 1H), 8.26 (s, 1H), 8.24 (s, 1H), 7.56 (s, 1H), 7.54 (s, 1H), 2.71 (s, 3H), 2.63 (s, 3H).

Synthesis Example 3 Preparation of 8-chloro-N-[(2-chloro-5-ethylphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide Step A: Preparation of 2-chloro-5-ethylbenzenesulfonyl chloride

Chlorosulfonic acid (4.0 mL, 59 mmol) was cooled to 0° C. and 1-chloro-4-ethylbenzene (1.0 mL, 7.5 mmol) was added dropwise over 30 min. The reaction mixture was stirred for 45 min at 0° C., poured with stirring onto 125 mL of crushed ice, and then extracted with ethyl acetate (2×100 mL). The ethyl acetate layers were combined, washed with water (100 mL), and dried over magnesium sulfate. The ethyl acetate was concentrated under reduced pressure to obtain an oil determined to be approximately a 1:1 mixture of isomers. This mixture was chromatographed on silica gel eluting with a hexane/ethyl acetate gradient to afford 0.41 g of the title compound. ¹H NMR (CDCl₃) δ 7.97 (s, 1H), 7.53 (d, 1H), 7.49 (d, 1H), 2.75 (q, 2H), 1.29 (t, 3H).

Step B: Preparation of 2-chloro-5-ethylbenzenesulfonamide

To a solution of 2-chloro-5-ethylbenzenesulfonyl chloride (0.41 g, 1.7 mmol, the product of Step A) in tetrahydrofuran (30 mL) was added 30% ammonium hydroxide (0.41 mL, 3.5 mmol) dropwise. The reaction mixture was stirred for 15 minutes, during which time a suspension formed. To this mixture water (10 mL) was added, and the tetrahydrofuran was evaporated under reduced pressure to precipitate a solid. The solid was dissolved in diethyl ether, dried over magnesium sulfate, and concentrated under reduced pressure. Diethyl ether and hexane were added to precipitate a solid. The solid was isolated by filtration to afford 190 mg of the title compound. ¹H NMR (CDCl₃) δ 7.95 (s, 1H), 7.43 (d, 1H), 7.35 (d, 1H), 5.08 (br s, 2H), 2.71 (q, 2H), 1.25 (t, 3H).

Step C: Preparation of 8-chloro-N-[(2-chloro-5-ethylphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide

To a solution of 8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid (100 mg, 0.38 mmol, prepared as described in Example 1 Step C) in a 1:1 mixture of t-butanol (5 mL) and dichloromethane (5 mL) was added 4-(dimethylamino)pyridine (138 mg, 1.1 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (182 mg, 0.95 mmol). The reaction mixture was stirred for 15 min, 2-chloro-5-ethylbenzenesulfonamide (74 mg, 0.34 mmol) was added, and the reaction mixture was stirred at room temperature overnight. Dichloromethane (100 mL) was then added, the mixture was washed with 1 N hydrochloric acid (3×50 mL), and the organic phase was dried over magnesium sulfate and concentrated under reduced pressure to afford a solid. The solid was rinsed with diethyl ether to afford 84 mg of the title compound, a compound of the present invention, as a solid, m.p. 214-215° C. ¹H NMR (CDCl₃) δ 10.12 (br s, 1H), 8.45 (s, 1H), 8.26 (s, 1H), 8.20 (s, 1H), 7.53 (s, 1H), 7.40 (s, 2H), 2.77 (q, 2H), 1.30 (t, 3H).

Synthesis Example 4 Preparation of 8-chloro-N-[(1-ethyl-3-methyl-1H-pyrazol-4-yl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide Step A: Preparation of 1-ethyl-3-methyl-1H-pyrazole-4-sulfonamide

To a solution of 1-ethyl-3-methyl-1H-pyrazole-4-sulfonylchloride (0.154 g, 0.73 mmol, Matrix Scientific) in tetrahydrofuran (10 mL) was added dropwise an aqueous solution of 30% ammonium hydroxide (0.20 mL, 1.7 mmol). The reaction mixture was stirred for 1 hour, water (2 mL) was added, and the solvent was concentrated under reduced pressure to precipitate a solid. The solid was isolated by filtration, rinsed with water, and dried to afford 41 mg of the title compound. ¹H NMR (CDCl₃) δ 7.80 (s, 1H), 4.75 (br s, 1H), 4.11 (q, 2H), 2.44 (s, 3H), 1.49 (t, 3H).

Step B: Preparation of 8-chloro-N-[(1-ethyl-3-methyl-1H-pyrazol-4-yl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide

To a solution of 8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid (63 mg, 0.24 mmol, prepared as described in Example 1 Step C) in a 1:1 mixture of t-butanol (5 mL) and dichloromethane (5 mL) was added 4-(dimethylamino)pyridine (88 mg, 0.71 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (117 mg, 0.60 mmol). The reaction mixture was stirred for 15 min, after which time 1-ethyl-3-methyl-1H-pyrazole-4-sulfonamide (41 mg, 0.22 mmol, the product of Step A) was added, and the reaction mixture was stirred at room temperature overnight. Dichloromethane (100 mL) was added and the mixture was washed with 1 N hydrochloric acid (3×50 mL). The organic phase was separated, dried over magnesium sulfate, and concentrated under reduced pressure to afford a solid. The solid was suspended in a mixture of diethyl ether and hexane, filtered, and dried to afford 25 mg of the title compound, a compound of the present invention, as a solid, m.p. 189-190° C. ¹H NMR (CDCl₃) δ 9.85 (br s, 1H), 8.47 (s, 1H), 8.29 (s, 1H), 8.10 (s, 1H), 7.53 (s, 1H), 4.14 (q, 2H), 2.51 (s, 3H), 1.51 (t, 3H).

Synthesis Example 5 Preparation of 8-chloro-N-[(3-chloro-1-ethyl-1H-pyrazol-4-yl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide Step A: Preparation of 1-ethyl-1H-pyrazol-3-ylamine

To a solution of potassium carbonate (2.76 g, 20.0 mmol) in water (10 mL) was added ethyl hydrazine oxalate (3.0 g, 20 mmol) followed by the dropwise addition of 2-chloroacrylonitrile (1.6 mL, 20 mmol) over 30 min. The mixture was stirred at room temperature for 2 h, and then heated at 50° C. for 2 h. The reaction mixture was cooled and extracted with ethyl acetate (2×100 mL). The ethyl acetate was dried over magnesium sulfate and evaporated under reduced pressure to obtain an oil. The oil was chromatographed on silica gel eluting with hexane and ethyl acetate as eluent to afford 540 mg of the title compound. ¹H NMR (CDCl₃) δ 7.12 (d, 1H) 5.57 (d, 1H), 3.96 (q, 2H), 3.59 (br s, 1H), 1.42 (t, 3H).

Step B: Preparation of 3-chloro-1-ethyl-1H-pyrazole

To a solution of 1-ethyl-1H-pyrazol-3-ylamine (0.54 g, 4.86 mmol, the product of Step A) in concentrated hydrochloric acid (5 mL) at 0° C. was added a solution of sodium nitrite (369 mg, 5.35 mmol) in water (1 mL) dropwise while maintaining the temperature below 10° C. The reaction mixture was stirred for 30 min, a solution of copper (I) chloride in concentrated hydrochloric acid (2 mL) was added dropwise, and the resulting reaction mixture was then heated to 60° C. A catalytic amount of copper chloride was added at 60° C. (initiating the evolution of gas). The reaction mixture was stirred for 5 min and then poured onto 100 mL of crushed ice containing 50% sodium hydroxide (5 mL) and stirred well. The aqueous mixture was extracted with dichloromethane (2×150 mL), and the organic layer was separated, washed with water, dried over magnesium sulfate and concentrated under reduced pressure to obtain 0.42 g of the title compound. ¹H NMR (CDCl₃) δ 7.31 (d, 1H), 6.15 (d, 1H), 4.11 (q, 2H), 1.47 (t, 3H).

Step C: Preparation of 3-chloro-1-ethyl-1H-pyrazole-4-sulfonyl chloride

3-Chloro-1-ethyl-1H-pyrazole (0.42 g, 3.2 mmol, the product of Step B) was added to chlorosulfonic acid (2.0 mL, 30 mmol) at room temperature and the mixture was slowly warmed to 100° C., and then heated at 100-110° C. for 2 hours. The reaction mixture was cooled, poured with stirring onto 150 mL of crushed ice, and extracted into diethyl ether (2×100 mL). The ether extracts were combined, washed with water (100 mL), dried over magnesium sulfate and concentrated under reduced pressure to obtain 0.5 g of the title compound as an oil. ¹H NMR (CDCl₃) δ 8.00 (s, 1H), 4.20 (q, 2H), 1.56 (t, 3H).

Step D: Preparation of 3-chloro-1-ethyl-1H-pyrazole-4-sulfonamide

To a solution of 3-chloro-1-ethyl-1H-pyrazole-4-sulfonyl chloride (0.5 g, 2.2 mmol, the product of Step D) in tetrahydrofuran (20 mL) was added 30% ammonium hydroxide (3.0 mL, 24 mmol) dropwise. The reaction mixture was heated to boiling with a heat gun and then stirred for 30 min. Tetrahydrofuran was removed under reduced pressure, water (50 mL) was added, the reaction mixture was extracted into ethyl acetate (2×100 mL). The ethyl acetate was dried over magnesium sulfate and concentrated under reduced pressure to afford a solid. The solid was washed with hexane, and dried to afford 282 mg of the title compound. ¹H NMR (CDCl₃) δ 7.84 (s, 1H), 4.94 (br s, 1H), 4.15 (q, 2H), 1.51 (t, 3H).

Step E: Preparation of 8-chloro-N-[(3-chloro-1-ethyl-1H-pyrazol-4-yl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide

To a solution of 8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid (110 mg, 0.42 mmol, prepared as described in Example 1 Step C) in a 1:1 mixture of t-butanol (5 mL) and dichloromethane (5 mL) was added 4-(dimethylamino)pyridine (152 mg, 1.25 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (96 mg, 0.5 mmol). The reaction mixture was stirred for 15 min after which time 3-chloro-1-ethyl-1H-pyrazole-4-sulfonamide (81 mg, 0.38 mmol, the product of Step D) was added and stirring was continued at room temperature overnight. Dichloromethane (100 mL) was then added and the mixture was extracted with 1 N hydrochloric acid (3×50 mL). The separated organic phases were combined, dried over magnesium sulfate, and concentrated under reduced pressure to afford a solid. The solid was suspended in a mixture of diethyl ether and hexane and filtered to afford 85 mg of the title compound, a compound of the present invention, as a solid, m.p. 184-185° C. ¹H NMR (CDCl₃) δ 9.96 (br s, 1H), 8.47 (s, 1H), 8.29 (s, 1H), 8.16 (s, 1H), 7.54 (s, 1H), 4.17 (q, 2H), 1.54 (t, 3H).

Synthesis Example 6 Preparation of 8-bromo-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)-imidazo[1,2-a]pyridine-2-carboxamide Step A: Preparation of 8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid

To a solution of 2-amino-3-bromo-5-(trifluoromethyl)pyridine (10.0 g, 41.5 mmol) in 1,2 dimethoxyethane (300 mL) at room temperature was added ethyl bromopyruvate (9.889 g, 45.64 mmol) dropwise. The reaction mixture was heated to reflux for 18 h. The 1,2-dimethoxyethane was removed under reduced pressure and the residual solid was recrystallized from 1-chlorobutane. The solid was isolated by filtration and dried to afford an off-white solid, 8-bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid, ethyl ester (11.044 g).

The solid obtained above was dissolved in tetrahydrofuran (150 mL) and a solution of LiOH (2.353 g, 98.29 mmol) in water (100 mL) was added. The reaction mixture was stirred at room temperature for 4 h. The tetrahydrofuran was removed under reduced pressure to provide an aqueous solution which was cooled to 5° C. Dilute HCl was added dropwise until a pH <5.0 was achieved. After several minutes a solid began to precipitate from the solution. The solid was collected by filtration, washed once with water (50 mL), and dried in a vacuum oven for 18 h at 80° C. to afford 8.632 g of the title compound as a solid. ¹H NMR (dmso-d₆) δ 13.17 (br s, 1H), 9.31 (s, 1H), 8.69 (s, 1H), 8.03 (s, 1H).

Step B: Preparation of 8-bromo-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide

To the product of Step A (200 mg, 0.647 mmol) was added a solution of 4-(dimethylamino)pyridine (237 mg, 1.94 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (309 mg, 1.62 mmol) in a 1:1 mixture of t-butanol (5 mL) and dichloromethane (5 mL). The reaction mixture was stirred for 15 min, 2-chloro-5-methoxybenzenesulfonamide (129 mg, 0.582 mmol) was added, and the reaction mixture was stirred at room temperature overnight. Dichloromethane (200 mL) was then added, the mixture was extracted with 1 N hydrochloric acid (3×100 mL), and the separated organic phases were combined, dried over magnesium sulfate, and concentrated under reduced pressure to afford a solid. The solid was rinsed with diethyl ether to afford 234 mg of the title compound, a compound of the present invention, as a white solid, m.p. 191-192° C. ¹H NMR (CDCl₃) δ 10.1 (br s, 1H), 8.51 (s, 1H), 8.30 (s, 1H), 7.87 (d, 1H), 7.72 (s, 1H), 7.38 (d, 1H), 7.08 (dd, 1H) 3.91 (s, 3H).

Synthesis Example 7 Preparation of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-3-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide Step A: Preparation of 3-bromo-2-oxo-butyric acid ethyl ester

2-Oxo-butyric acid (10.0 g, 97.2 mmol) was dissolved in ethanol (100 mL) and p-toluene sulfonic acid mono hydrate (0.1 g) was added. The reaction mixture was heated to reflux for 48 h. After cooling the reaction mixture to room temperature, the ethanol was removed under reduced pressure to give 11.4 g of 2-oxo-butyric acid ethyl ester.

The 2-oxo-butyric acid ethyl ester prepared above was dissolved in chloroform (100 mL) and bromine (20.964 g, 131.19 mmol) was added dropwise at room temperature. The reaction mixture was allowed to stir for 18 h. Concentration of the reaction mixture under reduced pressure provided 12.0 g of the title compound as an orange oil. ¹H NMR (CDCl₃) δ 4.39 (q, 2H), 4.32 (q, 1H), 1.88 (d, 3H), 1.39 (t, 3H).

Step B: Preparation of 8-chloro-3-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid

To a solution of 2-amino-3-chloro-5-(trifluoromethyl)pyridine (11.3 g, 57.5 mmol) in dioxane (200 mL) at room temperature was added dropwise 3-bromo-2-oxo-butyric acid ethyl ester (12.017 g, 57.49 mmol, the product of Step A). The reaction mixture was heated to reflux for 24 h, cooled, and the dioxane was removed under reduced pressure. Chromatography on silica gel eluting with a hexane/ethyl acetate gradient afforded 17.3 g of 8-chloro-3-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester as a solid.

The solid prepared above was dissolved in tetrahydrofuran (100 mL) and a solution of LiOH (3.365 g, 140.8 mmol) in water (50 mL) was added. The reaction mixture was stirred at room temperature for 18 h. The tetrahydrofuran was removed under reduced pressure to provide an aqueous solution which was cooled to 5° C. Dilute HCl was added dropwise until a pH <5.0 was achieved. After several minutes a solid began to precipitate. The solid was collected by filtration, washed with water (50 mL), and dried at 80° C. in a vacuum oven for 18 h to afford 15.7 g of a solid. ¹H NMR (dmso-d₆) δ 13.1 (br s, 1H), 8.84 (s, 1H), 7.80 (s, 1H), 2.82 (s, 3H).

Step C: Preparation of 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-3-methyl-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide

To the carboxylic acid prepared in Step B (200 mg, 0.72 mmol) was added a solution of 4-(dimethylamino)pyridine (262 mg, 2.15 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (344 mg, 1.79 mmol) in a 1:1 solvent mixture of t-butanol (5 mL) and dichloromethane (5 mL). The reaction mixture was stirred for 15 minutes, 2-chloro-5-methoxybenzenesulfonamide (143 mg, 0.65 mmol) was added, and the reaction mixture was stirred at room temperature overnight. Dichloromethane (200 mL) was then added, the mixture was extracted with 1 N hydrochloric acid (3×100 mL), and the separated organic layers were combined, dried over magnesium sulfate, and concentrated under reduced pressure to afford a solid. The solid was rinsed with diethyl ether to afford 118 mg of the title compound, a compound of the present invention, as a white solid, m.p. 222-223° C. ¹H NMR (dmso-d₆) δ 10.0 (br s, 1H), 8.94 (s, 1H), 7.96 (s, 1H), 7.65 (d, 1H), 7.59 (d, 1H), 7.30 (dd, 1H), 3.87 (s, 3H) 2.71 (s, 3H).

By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 22 can be prepared. The following abbreviations are used in the Tables which follow: Me means methyl, Et means ethyl, OMe means methoxy, SMe means methylthio, and NMe₂ means dimethylamino.

TABLE 1

R^(1a) is CF₃, R^(1b) is Cl, R² and R³ are H R^(a) R^(b) R^(c) R^(d) R^(e) H H H H H H Me H H H H Et H H H H F H H H H Cl H H H H Br H H H H CF₃ H H H H cyano H H H H OMe H H H H SMe H H H F H H H H F Me H H H F Et H H H F F H H H F Cl H H H F Br H H H F CF₃ H H H F cyano H H H F OMe H H H F SMe H H H Br H H H H Br Me H H H Br Et H H H Br F H H H Br Cl H H H Br Br H H H Br CF₃ H H H Br cyano H H H Br OMe H H H Br SMe H H H cyano H H H H cyano Me H H H cyano Et H H H cyano F H H H cyano Cl H H H H H H H H H H Me H H H H Et H H H H F H H H H Cl H H H H Br H H H H CF₃ H H H H cyano H H H H OMe H H H H SMe H H F H H H H F H Me H H F H Et H H F H F H H F H Cl H H F H Br H H F H CF₃ H H F H cyano H H F H OMe H H F H SMe H H Br H H H H Br H Me H H Br H Et H H Br H F H H Br H Cl H H Br H Br H H Br H CF₃ H H Br H cyano H H Br H OMe H H Br H SMe H H cyano H H H H cyano H Me H H cyano H Et H H cyano H F H H cyano H Cl H H H H H H H H H H Me H H H H Et H H H H F H H H H Cl H H H H Br H H H H CF₃ H H H H cyano H H H H OMe H H H H SMe H H H H CO₂Me H H H H C(O)Me H H H H NMe₂ H H H H nitro H F H H H H F H H Me H F H H Et H F H H F H F H H Cl H F H H Br H F H H CF₃ H F H H cyano H F H H OMe H F H H SMe H F H H CO₂Me H F H H C(O)Me H F H H NMe₂ H F H H nitro H Br H H H H Br H H Me H Br H H Et H Br H H F H Br H H Cl H Br H H Br H Br H H CF₃ H Br H H cyano H Br H H OMe H Br H H SMe H Br H H CO₂Me H Br H H C(O)Me H Br H H NMe₂ H Br H H nitro H cyano H H H H cyano H H Me H cyano H H Et H cyano H H F H cyano H H Cl H cyano H H Br H cyano H H CF₃ H H H Me H H H H Me Me H H H Me Et H H H Me F H H H Me Cl H H H Me Br H H H Me CF₃ H H H Me cyano H H H Me OMe H H H Me SMe H H H Me CO₂Me H H H Me C(O)Me H H H Me NMe₂ H H H Me nitro H F H Me H H F H Me Me H F H Me Et H F H Me F H F H Me Cl H F H Me Br H F H Me CF₃ H F H Me cyano H F H Me OMe H F H Me SMe H F H Me CO₂Me H F H Me C(O)Me H F H Me NMe₂ H F H Me nitro H Br H Me H H Br H Me Me H Br H Me Et H Br H Me F H Br H Me Cl H Br H Me Br H Br H Me CF₃ H Br H Me cyano H Br H Me OMe H Br H Me SMe H Br H Me CO₂Me H Br H Me C(O)Me H Br H Me NMe₂ H Br H Me nitro H cyano H Me H H cyano H Me Me H cyano H Me Et H cyano H Me F H cyano H Me Cl H cyano H Me Br H cyano H Me CF₃ H H H Cl H H H H Cl Me H H H Cl Et H H H Cl F H H H Cl Cl H H H Cl Br H H H Cl CF₃ H H H Cl cyano H H H Cl OMe H H H Cl SMe H H H Cl CO₂Me H H H Cl C(O)Me H H H Cl NMe₂ H H H Cl nitro H F H Cl H H F H Cl Me H F H Cl Et H F H Cl F H F H Cl Cl H F H Cl Br H F H Cl CF₃ H F H Cl cyano H F H Cl OMe H F H Cl SMe H F H Cl CO₂Me H F H Cl C(O)Me H F H Cl NMe₂ H F H Cl nitro H Br H Cl H H Br H Cl Me H Br H Cl Et H Br H Cl F H Br H Cl Cl H Br H Cl Br H Br H Cl CF₃ H Br H Cl cyano H Br H Cl OMe H Br H Cl SMe H Br H Cl CO₂Me H Br H Cl C(O)Me H Br H Cl NMe₂ H Br H Cl nitro H cyano H Cl H H cyano H Cl Me H cyano H Cl Et H cyano H Cl F H cyano H Cl Cl H cyano H Cl Br H cyano H Cl CF₃ H H H cyano H H H H cyano Me H H H cyano Et H H H cyano F H H H cyano Cl H H H cyano Br H H H cyano CF₃ H H H cyano cyano H H H cyano OMe H H H cyano SMe H H H cyano CO₂Me H H H cyano C(O)Me H H H cyano NMe₂ H H H cyano nitro H F H cyano H H F H cyano Me H F H cyano Et H F H cyano F H F H cyano Cl H F H cyano Br H F H cyano CF₃ H F H cyano cyano H F H cyano OMe H F H cyano SMe H F H cyano CO₂Me H F H cyano C(O)Me H F H cyano NMe₂ H F H cyano nitro H Br H cyano H H Br H cyano Me H Br H cyano Et H Br H cyano F H Br H cyano Cl H Br H cyano Br H Br H cyano CF₃ H Br H cyano cyano H Br H cyano OMe H Br H cyano SMe H Br H cyano CO₂Me H Br H cyano C(O)Me H Br H cyano NMe₂ H Br H cyano nitro H cyano H cyano H H cyano H cyano Me H cyano H cyano Et H cyano H cyano F H cyano H cyano Cl H cyano H cyano Br H cyano H cyano CF₃ H H H H H H H H H H Me H H H H F H H H H Cl H H H H Br F H H H H F H H H Me F H H H F F H H H Cl F H H H Br Br H H H H Br H H H Me Br H H H F Br H H H Cl Br H H H Br cyano H H H H cyano H H H Me Cl H H OCF₃ H OCF₃ H H Cl H Me H H H H Me Me H H H Me Et H H H Me F H H H Me Cl H H H Me Br H H H Me CF₃ H H H Me cyano H H H Me OMe H H H Me SMe H H H Cl H H H H Cl Me H H H Cl Et H H H Cl F H H H Cl Cl H H H Cl Br H H H Cl CF₃ H H H Cl cyano H H H Cl OMe H H H Cl SMe H H H CF₃ H H H H CF₃ Me H H H CF₃ Et H H H CF₃ F H H H CF₃ Cl H H H CF₃ Br H H H CF₃ CF₃ H H H CF₃ cyano H H H CF₃ OMe H H H CF₃ SMe H H H cyano Br H H H cyano CF₃ H H H cyano cyano H H H cyano OMe H H H cyano SMe H H H Me H H H H Me H Me H H Me H Et H H Me H F H H Me H Cl H H Me H Br H H Me H CF₃ H H Me H cyano H H Me H OMe H H Me H SMe H H Cl H H H H Cl H Me H H Cl H Et H H Cl H F H H Cl H Cl H H Cl H Br H H Cl H CF₃ H H Cl H cyano H H Cl H OMe H H Cl H SMe H H CF₃ H H H H CF₃ H Me H H CF₃ H Et H H CF₃ H F H H CF₃ H Cl H H CF₃ H Br H H CF₃ H CF₃ H H CF₃ H cyano H H CF₃ H OMe H H CF₃ H SMe H H cyano H Br H H cyano H CF₃ H H cyano H cyano H H cyano H OMe H H cyano H SMe H H Me H H H H Me H H Me H Me H H Et H Me H H F H Me H H Cl H Me H H Br H Me H H CF₃ H Me H H cyano H Me H H OMe H Me H H SMe H Me H H CO₂Me H Me H H C(O)Me H Me H H NMe₂ H Me H H nitro H Cl H H H H Cl H H Me H Cl H H Et H Cl H H F H Cl H H Cl H Cl H H Br H Cl H H CF₃ H Cl H H cyano H Cl H H OMe H Cl H H SMe H Cl H H CO₂Me H Cl H H C(O)Me H Cl H H NMe₂ H Cl H H nitro H CF₃ H H H H CF₃ H H Me H CF₃ H H Et H CF₃ H H F H CF₃ H H Cl H CF₃ H H Br H CF₃ H H CF₃ H CF₃ H H cyano H CF₃ H H OMe H CF₃ H H SMe H CF₃ H H CO₂Me H CF₃ H H C(O)Me H CF₃ H H NMe₂ H CF₃ H H nitro H cyano H H cyano H cyano H H OMe H cyano H H SMe H cyano H H CO₂Me H cyano H H C(O)Me H cyano H H NMe₂ H cyano H H nitro H Me H Me H H Me H Me Me H Me H Me Et H Me H Me F H Me H Me Cl H Me H Me Br H Me H Me CF₃ H Me H Me cyano H Me H Me OMe H Me H Me SMe H Me H Me CO₂Me H Me H Me C(O)Me H Me H Me NMe₂ H Me H Me nitro H Cl H Me H H Cl H Me Me H Cl H Me Et H Cl H Me F H Cl H Me Cl H Cl H Me Br H Cl H Me CF₃ H Cl H Me cyano H Cl H Me OMe H Cl H Me SMe H Cl H Me CO₂Me H Cl H Me C(O)Me H Cl H Me NMe₂ H Cl H Me nitro H CF₃ H Me H H CF₃ H Me Me H CF₃ H Me Et H CF₃ H Me F H CF₃ H Me Cl H CF₃ H Me Br H CF₃ H Me CF₃ H CF₃ H Me cyano H CF₃ H Me OMe H CF₃ H Me SMe H CF₃ H Me CO₂Me H CF₃ H Me C(O)Me H CF₃ H Me NMe₂ H CF₃ H Me nitro H cyano H Me cyano H cyano H Me OMe H cyano H Me SMe H cyano H Me CO₂Me H cyano H Me C(O)Me H cyano H Me NMe₂ H cyano H Me nitro H Me H Cl H H Me H Cl Me H Me H Cl Et H Me H Cl F H Me H Cl Cl H Me H Cl Br H Me H Cl CF₃ H Me H Cl cyano H Me H Cl OMe H Me H Cl SMe H Me H Cl CO₂Me H Me H Cl C(O)Me H Me H Cl NMe₂ H Me H Cl nitro H Cl H Cl H H Cl H Cl Me H Cl H Cl Et H Cl H Cl F H Cl H Cl Cl H Cl H Cl Br H Cl H Cl CF₃ H Cl H Cl cyano H Cl H Cl OMe H Cl H Cl SMe H Cl H Cl CO₂Me H Cl H Cl C(O)Me H Cl H Cl NMe₂ H Cl H Cl nitro H CF₃ H Cl H H CF₃ H Cl Me H CF₃ H Cl Et H CF₃ H Cl F H CF₃ H Cl Cl H CF₃ H Cl Br H CF₃ H Cl CF₃ H CF₃ H Cl cyano H CF₃ H Cl OMe H CF₃ H Cl SMe H CF₃ H Cl CO₂Me H CF₃ H Cl C(O)Me H CF₃ H Cl NMe₂ H CF₃ H Cl nitro H cyano H Cl cyano H cyano H Cl OMe H cyano H Cl SMe H cyano H Cl CO₂Me H cyano H Cl C(O)Me H cyano H Cl NMe₂ H cyano H Cl nitro H Me H cyano H H Me H cyano Me H Me H cyano Et H Me H cyano F H Me H cyano Cl H Me H cyano Br H Me H cyano CF₃ H Me H cyano cyano H Me H cyano OMe H Me H cyano SMe H Me H cyano CO₂Me H Me H cyano C(O)Me H Me H cyano NMe₂ H Me H cyano nitro H Cl H cyano H H Cl H cyano Me H Cl H cyano Et H Cl H cyano F H Cl H cyano Cl H Cl H cyano Br H Cl H cyano CF₃ H Cl H cyano cyano H Cl H cyano OMe H Cl H cyano SMe H Cl H cyano CO₂Me H Cl H cyano C(O)Me H Cl H cyano NMe₂ H Cl H cyano nitro H CF₃ H cyano H H CF₃ H cyano Me H CF₃ H cyano Et H CF₃ H cyano F H CF₃ H cyano Cl H CF₃ H cyano Br H CF₃ H cyano CF₃ H CF₃ H cyano cyano H CF₃ H cyano OMe H CF₃ H cyano SMe H CF₃ H cyano CO₂Me H CF₃ H cyano C(O)Me H CF₃ H cyano NMe₂ H CF₃ H cyano nitro H cyano H cyano cyano H cyano H cyano OMe H cyano H cyano SMe H cyano H cyano CO₂Me H cyano H cyano C(O)Me H cyano H cyano NMe₂ H cyano H cyano nitro H Me H H H H Me H H H Me Me H H H F Me H H H Cl Me H H H Br Cl H H H H Cl H H H Me Cl H H H F Cl H H H Cl Cl H H H Br CF₃ H H H H CF₃ H H H Me CF₃ H H H F CF₃ H H H Cl CF₃ H H H Br cyano H H H F cyano H H H Cl cyano H H H Br

TABLE 2 Table 2 is constructed the same as Table 1, except that R² is Cl. For example, the first compound in Table 2 wherein R^(1a) is CF₃, R^(1b) is Cl, R² is Cl, R³ and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 3 Table 3 is constructed the same as Table 1, except that R² is Br. For example, the first compound in Table 3 wherein R^(1a) is CF₃, R^(1b) is Cl, R² is Br, R³ and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 4 Table 4 is constructed the same as Table 1, except that R² is Me. For example, the first compound in Table 4 wherein R^(1a) is CF₃, R^(1b) is Cl, R² is Me, R³ and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 5 Table 5 is constructed the same as Table 1, except that R^(1a) and R^(1b) are H. For example, the first compound in Table 5 wherein R^(1a) is H, R^(1b) is H, and R², R³ and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 5a Table 5a is constructed the same as Table 1, except that R^(1a) is Cl and R^(1b) is H. For example, the first compound in Table 5a wherein R^(1a) is Cl, R^(1b) is H, and R², R³ and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 5b Table 5b is constructed the same as Table 1, except that R^(1a) is Br and R^(1b) is H. For example, the first compound in Table 5b wherein R^(1a) is Br, R^(1b) is H, and R², R³ and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 5c Table 5c is constructed the same as Table 1, except that R^(1b) is H. For example, the first compound in Table 5c wherein R^(1a) is CF₃, R^(1b) is H, and R², R³ and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 6 Table 6 is constructed the same as Table 1, except that R^(1b) is Br. For example, the first compound in Table 6 wherein R^(1a) is CF₃, R^(1b) is Br, and R², R³ and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 6a Table 6 is constructed the same as Table 1, except that R^(1b) is F. For example, the first compound in Table 6 wherein R^(1a) is CF₃, R^(1b) is F, and R², R³ and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 7 Table 7 is constructed the same as Table 1, except that R^(1a) and R^(1b) are Cl. For example, the first compound in Table 7 wherein R^(1a) and R^(1b) are Cl, and R², R³ and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 8 Table 8 is constructed the same as Table 1, except that R^(1a) and R^(1b) are Br. For example, the first compound in Table 8 wherein R^(1a) and R^(1b) are Br, and R², R³ and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 9 Table 9 is constructed the same as Table 1, except that R³ is Me. For example, the first compound in Table 9 wherein R^(1a) is CF₃, R^(1b) is Cl, R³ is Me, and R² and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 10 Table 10 is constructed the same as Table 1, except that R³ is Et. For example, the first compound in Table 10 wherein R^(1a) is CF₃, R^(1b) is Cl, R³ is Et, and R² and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 11 Table 11 is constructed the same as Table 1, except that R³ is propargyl (i.e. CH₂C≡CH). For example, the first compound in Table 11 wherein R^(1a) is CF₃, R^(1b) is Cl, R³ is propargyl, and R² and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 12 Table 12 is constructed the same as Table 1, except that R³ is benzyl (i.e. CH₂C₆H₅). For example, the first compound in Table 12 wherein R^(1a) is CF₃, R^(1b) is Cl, R³ is benzyl, and R² and R^(a) through R^(e) are H is the structure shown immediately below.

TABLE 13

R^(a) R^(b) R^(c) H H H H H Me H H Cl H H Br H Me H H Me Me H Me Cl H Me Br H Et H H Et Me H Et Cl H Et Br H Cl H H Cl Me H Cl Cl H Cl Br Br H H Br H Me Br H Cl Br H Br Br Me H Br Me Me Br Me Cl Br Me Br Br Et H Br Et Me Br Et Cl Br Et Br Br Cl H Br Cl Me Br Cl Cl Br Cl Br Me H H Me H Me Me H Cl Me H Br Me Me H Me Me Me Me Me Cl Me Me Br Me Et H Me Et Me Me Et Cl Me Et Br Me Cl H Me Cl Me Me Cl Cl Me Cl Br Et H H Et H Me Et H Cl Et H Br Et Me H Et Me Me Et Me Cl Et Me Br Et Et H Et Et Me Et Et Cl Et Et Br Et Cl H Et Cl Me Et Cl Cl Et Cl Br Cl H H Cl H Me Cl H Cl Cl H Br Cl Me H Cl Me Me Cl Me Cl Cl Me Br Cl Et H Cl Et Me Cl Et Cl Cl Et Br Cl Cl H Cl Cl Me Cl Cl Cl Cl Cl Br

TABLE 14

R^(a) R^(b) R^(c) H H H H H Me H H Cl H Me H H Me Me H Me Cl H Et H H Et Me H Et Cl Et H H Et H Me Et H Cl Et Me H Et Me Me Et Me Cl Et Et H Et Et Me Et Et Cl Me H H Me H Me Me H Cl Me Me H Me Me Me Me Me Cl Me Et H Me Et Me Me Et Cl Br H H Br H Me Br H Cl Br Me H Br Me Me Br Me Cl Br Et H Br Et Me Br Et Cl Cl H H Cl H Me Cl H Cl Cl Me H Cl Me Me Cl Me Cl Cl Et H Cl Et Me Cl Et Cl

TABLE 15

R^(a) R^(b) H H H Me H Cl Me H Me Me Me Cl Cl H Cl Me Cl Cl

TABLE 16

R^(a) R^(b) H H H Me H Cl Me H Me Me Me Cl Cl H Cl Me Cl Cl

TABLE 17

R^(a) R^(b) R^(c) H H Me H H Et H H i-Pr H H n-Pr Br H Me Br H Et Br H i-Pr Br H n-Pr Cl Me Me Cl Me Et Cl Me i-Pr Cl Me n-Pr Me Cl Me Me Cl Et Me Cl i-Pr Me Cl n-Pr H Br Me H Br Et H Br i-Pr H Br n-Pr Br Br Me Br Br Et Br Br i-Pr Br Br n-Pr Me H Me Me H Et Me H i-Pr Me H n-Pr H Me Me H Me Et H Me i-Pr H Me n-Pr Br Me Me Br Me Et Br Me i-Pr Br Me n-Pr Cl Cl Me Cl Cl Et Cl Cl i-Pr Cl Cl n-Pr Me Br Me Me Br Et Me Br i-Pr Me Br n-Pr Cl H Me Cl H Et Cl H i-Pr Cl H n-Pr Me Me Me Me Me Et Me Me i-Pr Me Me n-Pr H Cl Me H Cl Et H Cl i-Pr H Cl n-Pr Br Cl Me Br Cl Et Br Cl i-Pr Br Cl n-Pr Cl Br Me Cl Br Et Cl Br i-Pr Cl Br n-Pr

TABLE 17a

R^(a) R^(b) R^(c) H H Me H H Et H H i-Pr H H n-Pr Br H Me Br H Et Br H i-Pr Br H n-Pr Cl Me Me Cl Me Et Cl Me i-Pr Cl Me n-Pr Me Cl Me Me Cl Et Me Cl i-Pr Me Cl n-Pr H Br Me H Br Et H Br i-Pr H Br n-Pr Br Br Me Br Br Et Br Br i-Pr Br Br n-Pr Me H Me Me H Et Me H i-Pr Me H n-Pr H Me Me H Me Et H Me i-Pr H Me n-Pr Br Me Me Br Me Et Br Me i-Pr Br Me n-Pr Cl Cl Me Cl Cl Et Cl Cl i-Pr Cl Cl n-Pr Me Br Me Me Br Et Me Br i-Pr Me Br n-Pr Cl H Me Cl H Et Cl H i-Pr Cl H n-Pr Me Me Me Me Me Et Me Me i-Pr Me Me n-Pr H Cl Me H Cl Et H Cl i-Pr H Cl n-Pr Br Cl Me Br Cl Et Br Cl i-Pr Br Cl n-Pr Cl Br Me Cl Br Et Cl Br i-Pr Cl Br n-Pr

TABLE 17b

R^(a) R^(b) R^(c) H H Me H H Et H H i-Pr H H n-Pr Br H Me Br H Et Br H i-Pr Br H n-Pr Cl Me Me Cl Me Et Cl Me i-Pr Cl Me n-Pr Me Cl Me Me Cl Et Me Cl i-Pr Me Cl n-Pr H Br Me H Br Et H Br i-Pr H Br n-Pr Br Br Me Br Br Et Br Br i-Pr Br Br n-Pr Me H Me Me H Et Me H i-Pr Me H n-Pr H Me Me H Me Et H Me i-Pr H Me n-Pr Br Me Me Br Me Et Br Me i-Pr Br Me n-Pr Cl Cl Me Cl Cl Et Cl Cl i-Pr Cl Cl n-Pr Me Br Me Me Br Et Me Br i-Pr Me Br n-Pr Cl H Me Cl H Et Cl H i-Pr Cl H n-Pr Me Me Me Me Me Et Me Me i-Pr Me Me n-Pr H Cl Me H Cl Et H Cl i-Pr H Cl n-Pr Br Cl Me Br Cl Et Br Cl i-Pr Br Cl n-Pr Cl Br Me Cl Br Et Cl Br i-Pr Cl Br n-Pr

TABLE 18

R^(a) R^(b) H H H Cl H Me H Et H i-Pr H n-Pr H OMe Me H Me Cl Me Me Me Et Me i-Pr Me n-Pr Me OMe Cl H Cl Cl Cl Me Cl Et Cl i-Pr Cl n-Pr Cl OMe Br H Br Cl Br Me Br Et Br i-Pr Br n-Pr Br OMe

TABLE 19

R^(a) R^(b) R^(c) H H Me H H Et H H i-Pr H H n-Pr Br H Me Br H Et Br H i-Pr Br H n-Pr Cl Me Me Cl Me Et Cl Me i-Pr Cl Me n-Pr Me Cl Me Me Cl Et Me Cl i-Pr Me Cl n-Pr H Br Me H Br Et H Br i-Pr H Br n-Pr Br Br Me Br Br Et Br Br i-Pr Br Br n-Pr Me H Me Me H Et Me H i-Pr Me H n-Pr H Me Me H Me Et H Me i-Pr H Me n-Pr Br Me Me Br Me Et Br Me i-Pr Br Me n-Pr Cl Cl Me Cl Cl Et Cl Cl i-Pr Cl Cl n-Pr Me Br Me Me Br Et Me Br i-Pr Me Br n-Pr Cl H Me Cl H Et Cl H i-Pr Cl H n-Pr Me Me Me Me Me Et Me Me i-Pr Me Me n-Pr H Cl Me H Cl Et H Cl i-Pr H Cl n-Pr Br Cl Me Br Cl Et Br Cl i-Pr Br Cl n-Pr Cl Br Me Cl Br Et Cl Br i-Pr Cl Br n-Pr

TABLE 20

R^(a) R^(b) R^(c) R^(d) R^(a) R^(b) R^(c) R^(d) Me H H H Cl H H H Me H H Me Cl H H Me Me H H OMe Cl H H OMe Me OMe H H Cl OMe H H Me OMe H Me Cl OMe H Me Me OMe H OMe Cl OMe H OMe Me H Me H Cl H Me H Me H Me Me Cl H Me Me Me H Me OMe Cl H Me OMe Me OMe Me H Cl OMe Me H Me OMe Me Me Cl OMe Me Me Me OMe Me OMe Cl OMe Me OMe Me Me H H Cl Me H H Me Me H Me Cl Me H Me Me Me H OMe Cl Me H OMe Me Me Me H Cl Me Me H Me Me Me Me Cl Me Me Me Me Me Me OMe Cl Me Me OMe Br H H H Br OMe Me H Br H H Me Br OMe Me Me Br H H OMe Br OMe Me OMe Br OMe H H Br Me H H Br OMe H Me Br Me H Me Br OMe H OMe Br Me H OMe Br H Me H Br Me Me H Br H Me Me Br Me Me Me Br H Me OMe Br Me Me OMe

TABLE 21

R^(a) R^(b) R^(c) R^(d) R^(a) R^(b) R^(c) R^(d) H H H H Me H H H H H H Me Me H H Me H H H CF₃ Me H H CF₃ H H H Cl Me H H Cl H H H Br Me H H Br H H Me H Me H Me H H H Me Me Me H Me Me H H Me CF₃ Me H Me CF₃ H H Me Cl Me H Me Cl H H Me Br Me H Me Br H Cl H H Me Cl H H H Cl H Me Me Cl H Me H Cl H CF₃ Me Cl H CF₃ H Cl H Cl Me Cl H Cl H Cl H Br Me Cl H Br H Cl Me H Me Cl Me H H Cl Me Me Me Cl Me Me H Cl Me CF₃ Me Cl Me CF₃ H Cl Me Cl Me Cl Me Cl H Cl Me Br Me Cl Me Br H Me H H Me Me H H H Me H Me Me Me H Me H Me H CF₃ Me Me H CF₃ H Me H Cl Me Me H Cl H Me H Br Me Me H Br H Me Me H Me Me Me H H Me Me Me Me Me Me Me H Me Me CF₃ Me Me Me CF₃ H Me Me Cl Me Me Me Cl H Me Me Br Me Me Me Br H CF₃ H H Me CF₃ H H H CF₃ H Me Me CF₃ H Me H CF₃ H CF₃ Me CF₃ H CF₃ H CF₃ H Cl Me CF₃ H Cl H CF₃ H Br Me CF₃ H Br H CF₃ Me H Me CF₃ Me H H CF₃ Me Me Me CF₃ Me Me H CF₃ Me CF₃ Me CF₃ Me CF₃ H CF₃ Me Cl Me CF₃ Me Cl H CF₃ Me Br Me CF₃ Me Br H OMe H H Me OMe H H H OMe H Me Me OMe H Me H OMe H CF₃ Me OMe H CF₃ H OMe H Cl Me OMe H Cl H OMe H Br Me OMe H Br H OMe Me H Me OMe Me H H OMe Me Me Me OMe Me Me H OMe Me CF₃ Me OMe Me CF₃ H OMe Me Cl Me OMe Me Cl H OMe Me Br Me OMe Me Br

TABLE 22

R^(a) R^(b) R^(c) R^(d) R^(a) R^(b) R^(c) R^(d) H H H H Me H H H H H H Me Me H H Me H H H Cl Me H H Cl H H Me H Me H Me H H H Me Me Me H Me Me H H Me Cl Me H Me Cl

A compound of this invention will generally be used as a parasitic nematode control active ingredient in a composition, i.e. formulation, with at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents, which serves as a carrier. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature.

Useful formulations include both liquid and solid compositions. Liquid compositions include solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspo-emulsions) and the like, which optionally can be thickened into gels. The general types of aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion and suspo-emulsion. The general types of nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.

The general types of solid compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible (“wettable”) or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient. An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for further formulation.

Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water. Spray volumes can range from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting. Liquid and solid formulations can be applied onto seeds of crops and other desirable vegetation as seed treatments before planting to protect developing roots and other subterranean plant parts and/or foliage through systemic uptake.

The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water- 0.001-90  0-99.999 0-15 soluble Granules, Tablets and Powders Oil Dispersions, Suspensions,    1-50 40-99    0-50 Emulsions, Solutions (including Emulsifiable Concentrates) Dusts    1-25 70-99    0-5  Granules and Pellets 0.001-95  5-99.999 0-15 High Strength Compositions   90-99 0-10   0-2 

Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose), silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J.

Liquid diluents include, for example, water, N,N-dimethylalkanamides (e.g., N,N-dimethylformamide), limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone), ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins), alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, triacetin, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, acetates such as isoamyl acetate, hexyl acetate, heptyl acetate, octyl acetate, nonyl acetate, tridecyl acetate and isobornyl acetate, other esters such as alkylated lactate esters, dibasic esters and γ-butyrolactone, and alcohols, which can be linear, branched, saturated or unsaturated, such as methanol, ethanol, n-propanol, isopropyl alcohol, n-butanol, isobutyl alcohol, n-hexanol, 2-ethylhexanol, n-octanol, decanol, isodecyl alcohol, isooctadecanol, cetyl alcohol, lauryl alcohol, tridecyl alcohol, oleyl alcohol, cyclohexanol, tetrahydrofurfuryl alcohol, diacetone alcohol and benzyl alcohol. Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C₆-C₂₂), such as plant seed and fruit oils (e.g, oils of olive, castor, linseed, sesame, corn (maize), peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel), animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil), and mixtures thereof. Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.

The solid and liquid compositions of the present invention often include one or more surfactants. When added to a liquid, surfactants (also known as “surface-active agents”) generally modify, most often reduce, the surface tension of the liquid. Depending on the nature of the hydrophilic and lipophilic groups in a surfactant molecule, surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.

Surfactants can be classified as nonionic, anionic or cationic. Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); block polymers prepared from ethylene oxide or propylene oxide and reverse block polymers where the terminal blocks are prepared from propylene oxide; ethoxylated fatty acids; ethoxylated fatty esters and oils; ethoxylated methyl esters; ethoxylated tristyrylphenol (including those prepared from ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); fatty acid esters, glycerol esters, lanolin-based derivatives, polyethoxylate esters such as polyethoxylated sorbitan fatty acid esters, polyethoxylated sorbitol fatty acid esters and polyethoxylated glycerol fatty acid esters; other sorbitan derivatives such as sorbitan esters; polymeric surfactants such as random copolymers, block copolymers, alkyd peg (polyethylene glycol) resins, graft or comb polymers and star polymers; polyethylene glycols (pegs); polyethylene glycol fatty acid esters; silicone-based surfactants; and sugar-derivatives such as sucrose esters, alkyl polyglycosides and alkyl polysaccharides.

Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of ethoxylated alcohols; sulfonates of amines and amides such as N,N-alkyltaurates; sulfonates of benzene, cumene, toluene, xylene, and dodecyl and tridecylbenzenes; sulfonates of condensed naphthalenes; sulfonates of naphthalene and alkyl naphthalene; sulfonates of fractionated petroleum; sulfosuccinamates; and sulfosuccinates and their derivatives such as dialkyl sulfosuccinate salts.

Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof); amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis-(2-hydroxyethyl)-alkylamine oxides.

Also useful for the present compositions are mixtures of nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants. Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon's Emulsifiers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.

Compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants). Such formulation auxiliaries and additives may control: pH (buffers), foaming during processing (antifoams such polyorganosiloxanes), sedimentation of active ingredients (suspending agents), viscosity (thixotropic thickeners), in-container microbial growth (antimicrobials), product freezing (antifreezes), color (dyes/pigment dispersions), wash-off (film formers or stickers), evaporation (evaporation retardants), and other formulation attributes. Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes. Examples of formulation auxiliaries and additives include those listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.

The compound of Formula 1 and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent. Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water. Active ingredient slurries, with particle diameters of up to 2,000 μm can be wet milled using media mills to obtain particles with average diameters below 3 μm. Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. Pat. No. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 μm range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill). Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. No. 4,144,050, U.S. Pat. No. 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. No. 5,180,587, U.S. Pat. No. 5,232,701 and U.S. Pat. No. 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see T. S. Woods, “The Formulator's Toolbox—Product Forms for Modern Agriculture” in Pesticide Chemistry and Bioscience, The Food-Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120-133. See also U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989; and Developments in formulation technology, PJB Publications, Richmond, UK, 2000.

In the following Examples, all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A-D. Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except where otherwise indicated.

Example A

High Strength Concentrate Compound 7 98.5% silica aerogel  0.5% synthetic amorphous fine silica  1.0%

Example B

Wettable Powder Compound 19 65.0% dodecylphenol polyethylene glycol ether  2.0% sodium ligninsulfonate  4.0% sodium silicoaluminate  6.0% montmorillonite (calcined) 23.0%

Example C

Granule Compound 30 10.0% attapulgite granules (low volatile matter, 0.71/0.30 mm; 90.0% U.S.S. No. 25-50 sieves)

Example D

Extruded Pellet Compound 170 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate  5.0% sodium alkylnaphthalenesulfonate  1.0% calcium/magnesium bentonite 59.0%

Example E

Emulsifiable Concentrate Compound 179 10.0% polyoxyethylene sorbitol hexoleate 20.0% C₆-C₁₀ fatty acid methyl ester 70.0%

Example F

Microemulsion Compound 180  5.0% polyvinylpyrrolidone-vinyl acetate copolymer 30.0% alkylpolyglycoside 30.0% glyceryl monooleate 15.0% water 20.0%

Example G

Seed Treatment Compound 68 20.00% polyvinylpyrrolidone-vinyl acetate copolymer  5.00% montan acid wax  5.00% calcium ligninsulfonate  1.00% polyoxyethylene/polyoxypropylene block copolymers  1.00% stearyl alcohol (POE 20)  2.00% polyorganosilane  0.20% colorant red dye  0.05% water 65.75%

Example H

Fertilizer Stick Compound 382  2.50% pyrrolidone-styrene copolymer  4.80% tristyrylphenyl 16-ethoxylate  2.30% talc  0.80% corn starch  5.00% Nitrophoska ® Permanent 15-9-15 slow-release fertilizer 36.00% (BASF) kaolin 38.00% water 10.60%

Compounds of this invention exhibit activity against a wide spectrum of parasitic pests. These pests include invertebrates inhabiting a variety of environments such as, for example, plant foliage, roots, soil, harvested crops or other foodstuffs, building structures or animal integuments. These pests include, for example, invertebrates feeding on foliage (including leaves, stems, flowers and fruits), seeds, wood, textile fibers or animal blood or tissues, and thereby causing injury or damage to, for example, growing or stored agronomic crops, forests, greenhouse crops, ornamentals, nursery crops, stored foodstuffs or fiber products, or houses or other structures or their contents, or being harmful to animal health or public health. Those skilled in the art will appreciate that not all compounds are equally effective against all growth stages of all pests.

These present compounds and compositions are thus useful agronomically for protecting field crops from parasitic nematodes, and also nonagronomically for protecting other horticultural crops and plants from phytophagous parasitic nematodes. This utility includes protecting crops and other plants (i.e. both agronomic and nonagronomic) that contain genetic material introduced by genetic engineering (i.e. transgenic) or modified by mutagenesis to provide advantageous traits. Examples of such traits include tolerance to herbicides, resistance to phytophagous pests (e.g., insects, mites, aphids, spiders, nematodes, snails, plant-pathogenic fungi, bacteria and viruses), improved plant growth, increased tolerance of adverse growing conditions such as high or low temperatures, low or high soil moisture, and high salinity, increased flowering or fruiting, greater harvest yields, more rapid maturation, higher quality and/or nutritional value of the harvested product, or improved storage or process properties of the harvested products. Transgenic plants can be modified to express multiple traits. Examples of plants containing traits provided by genetic engineering or mutagenesis include varieties of corn, cotton, soybean and potato expressing an insecticidal Bacillus thuringiensis toxin such as YIELD GARD®, KNOCKOUT®, STARLINK®, BOLLGARD®, NuCOTN® and NEWLEAF®, and herbicide-tolerant varieties of corn, cotton, soybean and rapeseed such as ROUNDUP READY®, LIBERTY LINK®, IMI®, STS® and CLEARFIELD®, as well as crops expressing N-acetyltransferase (GAT) to provide resistance to glyphosate herbicide, or crops containing the HRA gene providing resistance to herbicides inhibiting acetolactate synthase (ALS). The present compounds and compositions may interact synergistically with traits introduced by genetic engineering or modified by mutagenesis, thus enhancing phenotypic expression or effectiveness of the traits or increasing the parasitic nematode control effectiveness of the present compounds and compositions. In particular, the present compounds and compositions may interact synergistically with the phenotypic expression of proteins or other natural products toxic to parasitic nematodes to provide greater-than-additive control of these pests.

Compositions of this invention can also optionally comprise plant nutrients, e.g., a fertilizer composition comprising at least one plant nutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium, magnesium, iron, copper, boron, manganese, zinc, and molybdenum. Of note are compositions comprising at least one fertilizer composition comprising at least one plant nutrient selected from nitrogen, phosphorus, potassium, sulfur, calcium and magnesium. Compositions of the present invention which further comprise at least one plant nutrient can be in the form of liquids or solids. Of note are solid formulations in the form of granules, small sticks or tablets. Solid formulations comprising a fertilizer composition can be prepared by mixing the compound or composition of the present invention with the fertilizer composition together with formulating ingredients and then preparing the formulation by methods such as granulation or extrusion. Alternatively solid formulations can be prepared by spraying a solution or suspension of a compound or composition of the present invention in a volatile solvent onto a previous prepared fertilizer composition in the form of dimensionally stable mixtures, e.g., granules, small sticks or tablets, and then evaporating the solvent.

Compounds of this invention can exhibit activity against a wide spectrum of parasitic nematodes that live or grow inside or feed on plants (e.g., foliage, fruit, stems, roots or seeds) or animals and humans (e.g., vascular or digestive systems or other tissues) and therefore damage growing and stored agronomic crops, forestry, greenhouse crops, ornamentals and nursery crops, or afflict animal and human health. Crops of particular interest are fruiting vegetables such as solanaceous and cucurbit crops, plantation crops such as banana and coffee, root crops such as potatoes, onion and carrots, and field crops such as tobacco, peanut, cotton, sugarcane and soybean.

Compounds of this invention can have activity on members of both classes Adenophorea and Secernentea of the Phylum Nematoda, including economically important members of the orders Enoplida, Dorylaimida, Rhabditida, Strongylida, Ascarida, Oxyurida, Spirurida, Tylenchida and Aphelenchida, such as but not limited to economically important agricultural pests such as root-knot nematodes of the genus Meloidogyne, cyst nematodes of the genera Heterodera and Globodera, lesion nematodes of the genus Pratylenchus, reniform nematodes of the genus Rotylenchulus, burrowing nematodes of the genus Radopholus, sting nematodes of the genus Belonolaimus, spiral nematodes of the genera Helicotylenchus and Scutellonema, citrus nematodes of the genus Tylenchulus, stubby root nematodes of the genera Trichodorus and Paratrichodorus, dagger nematodes of the genus Xiphinema, stunt nematodes of the genus Tylenchorhynchus, needle nematodes of the genera Longidorus and Paralongidorus, lance nematodes of the genus Hoplolaimus, ring nematodes of the family Criconematidae, stem nematodes of the genera Ditylenchus and Anguina, and foliar/stem nematodes of the genera Aphelenchoides and Rhadinaphelenchus; and animal and human health parasites (i.e. economically important roundworms such as Strongylus vulgaris in horses, Toxocara canis in dogs, Haemonchus contortus in sheep, Dirofilaria immitis in dogs, etc.).

Of note is use of compounds of this invention for controlling southern root-knot nematode (Meloidogyne incognita). Those skilled in the art will appreciate that not all compounds are equally effective against all growth stages of all nematodes.

Compounds of this invention can also have activity on members of the Phylum Platyhelminthes, classes Cestoda (Tapeworms) and Trematoda (Flukes), including parasites (i.e. economically important flukes and tapeworms) afflicting animal and human health (e.g., Anoplocephala perfoliata in horses, Fasciola hepatica in ruminants, etc.).

Compounds of this invention can also be mixed with one or more other biologically active compounds or agents including insecticides, fungicides, nematocides, bactericides, acaricides, herbicides, herbicide safeners, growth regulators such as insect molting inhibitors and rooting stimulants, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants, other biologically active compounds or entomopathogenic bacteria, virus or fungi to form a multi-component pesticide giving an even broader spectrum of agronomic and nonagronomic utility. Thus the present invention also pertains to a composition comprising a compound of Formula 1, an N-oxide, or salt thereof, and an effective amount of at least one additional biologically active compound or agent and can further comprise at least one of surfactants, solid diluents or liquid diluents. For mixtures of the present invention, the other biologically active compounds or agents can be formulated together with the present compounds, including the compounds of Formula 1, to form a premix, or the other biologically active compounds or agents can be formulated separately from the present compounds, including the compounds of Formula 1, and the two formulations combined together before application (e.g., in a spray tank) or, alternatively, applied in succession.

Examples of such biologically active compounds or agents with which compounds of this invention can be formulated are insecticides such as abamectin, acephate, acequinocyl, acetamiprid, acrinathrin, amidoflumet, amitraz, avermectin, azadirachtin, azinphos-methyl, bifenthrin, bifenazate, bistrifluoron, borate, buprofezin, cadusafos, carbaryl, carbofuran, cartap, carzol, chlorantraniliprole, chlorfenapyr, chlorfluazuron, chlorpyrifos, chlorpyrifos-methyl, chromafenozide, clofentezin, clothianidin, cyantraniliprole, cyflumetofen, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, diafenthiuron, diazinon, dieldrin, diflubenzuron, dimefluthrin, dimehypo, dimethoate, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenbutatin oxide, fenothiocarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flonicamid, flubendiamide, flucythrinate, flufenerim, flufenoxuron, fluvalinate, tau-fluvalinate, fonophos, formetanate, fosthiazate, halofenozide, hexaflumuron, hexythiazox, hydramethylnon, imidacloprid, indoxacarb, insecticidal soaps, isofenphos, lufenuron, malathion, metaflumizone, metaldehyde, methamidophos, methidathion, methiodicarb, methomyl, methoprene, methoxychlor, metofluthrin, monocrotophos, methoxyfenozide, nitenpyram, nithiazine, novaluron, noviflumuron, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, profluthrin, propargite, protrifenbute, pymetrozine, pyrafluprole, pyrethrin, pyridaben, pyridalyl, pyrifluquinazon, pyriprole, pyriproxyfen, rotenone, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, sulprofos, tebufenozide, tebufenpyrad, teflubenzuron, tefluthrin, terbufos, tetrachlorvinphos, tetramethrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tolfenpyrad, tralomethrin, triazamate, trichlorfon, triflumuron, Bacillus thuringiensis delta-endotoxins, entomopathogenic bacteria, entomopathogenic viruses and entomopathogenic fungi.

Of note are insecticides such as abamectin, acetamiprid, acrinathrin, amitraz, avermectin, azadirachtin, bifenthrin, buprofezin, cadusafos, carbaryl, cartap, chlorantraniliprole, chlorfenapyr, chlorpyrifos, clothianidin, cyantraniliprole, cyfluthrin, beta-cyfluthrin, cyhalothrin, gamma-cyhalothrin, lambda-cyhalothrin, cypermethrin, alpha-cypermethrin, zeta-cypermethrin, cyromazine, deltamethrin, dieldrin, dinotefuran, diofenolan, emamectin, endosulfan, esfenvalerate, ethiprole, etofenprox, etoxazole, fenothiocarb, fenoxycarb, fenvalerate, fipronil, flonicamid, flubendiamide, flufenoxuron, fluvalinate, formetanate, fosthiazate, hexaflumuron, hydramethylnon, imidacloprid, indoxacarb, lufenuron, metaflumizone, methiodicarb, methomyl, methoprene, methoxyfenozide, nitenpyram, nithiazine, novaluron, oxamyl, pymetrozine, pyrethrin, pyridaben, pyridalyl, pyriproxyfen, ryanodine, spinetoram, spinosad, spirodiclofen, spiromesifen, spirotetramat, tebufenozide, tetramethrin, thiacloprid, thiamethoxam, thiodicarb, thiosultap-sodium, tralomethrin, triazamate, triflumuron, Bacillus thuringiensis delta-endotoxins, all strains of Bacillus thuringiensis and all strains of Nucleo polyhydrosis viruses.

One embodiment of biological agents for mixing with compounds of this invention include entomopathogenic bacteria such as Bacillus thuringiensis, and the encapsulated delta-endotoxins of Bacillus thuringiensis such as MVP® and MVPII® bioinsecticides prepared by the CellCap® process (CellCap®, MVP® and MVPII® are trademarks of Mycogen Corporation, Indianapolis, Ind., USA); entomopathogenic fungi such as green muscardine fungus; and entomopathogenic (both naturally occurring and genetically modified) viruses including baculovirus, nucleopolyhedro virus (NPV) such as Helicoverpa zea nucleopolyhedrovirus (HzNPV), Anagrapha falcifera nucleopolyhedrovirus (AfNPV); and granulosis virus (GV) such as Cydia pomonella granulosis virus (CpGV).

Of particular note is such a combination where the other invertebrate pest control active ingredient belongs to a different chemical class or has a different site of action than the compound of Formula 1. In certain instances, a combination with at least one other invertebrate pest control active ingredient having a similar spectrum of control but a different site of action will be particularly advantageous for resistance management. Thus, a composition of the present invention can further comprise at least one additional invertebrate pest control active ingredient having a similar spectrum of control but belonging to a different chemical class or having a different site of action. These additional biologically active compounds or agents include, but are not limited to, sodium channel modulators such as bifenthrin, cypermethrin, cyhalothrin, lambda-cyhalothrin, cyfluthrin, beta-cyfluthrin, deltamethrin, dimefluthrin, esfenvalerate, fenvalerate, indoxacarb, metofluthrin, profluthrin, pyrethrin and tralomethrin; cholinesterase inhibitors such as chlorpyrifos, methomyl, oxamyl, thiodicarb and triazamate; neonicotinoids such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid and thiamethoxam; insecticidal macrocyclic lactones such as spinetoram, spinosad, abamectin, avermectin and emamectin; GABA (γ-aminobutyric acid)-gated chloride channel antagonists such as avermectin or blockers such as ethiprole and fipronil; chitin synthesis inhibitors such as buprofezin, cyromazine, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron and triflumuron; juvenile hormone mimics such as diofenolan, fenoxycarb, methoprene and pyriproxyfen; octopamine receptor ligands such as amitraz; molting inhibitors and ecdysone agonists such as azadirachtin, methoxyfenozide and tebufenozide; ryanodine receptor ligands such as ryanodine, anthranilic diamides such as chlorantraniliprole, cyantraniliprole and flubendiamide; nereistoxin analogs such as cartap; mitochondrial electron transport inhibitors such as chlorfenapyr, hydramethylnon and pyridaben; lipid biosynthesis inhibitors such as spirodiclofen and spiromesifen; cyclodiene insecticides such as dieldrin or endosulfan; pyrethroids; carbamates; insecticidal ureas; and biological agents including nucleopolyhedro viruses (NPV), members of Bacillus thuringiensis, encapsulated delta-endotoxins of Bacillus thuringiensis, and other naturally occurring or genetically modified insecticidal viruses.

Further examples of biologically active compounds or agents with which compounds of this invention can be formulated are: fungicides such as acibenzolar, aldimorph, amisulbrom, azaconazole, azoxystrobin, benalaxyl, benomyl, benthiavalicarb, benthiavalicarb-isopropyl, binomial, biphenyl, bitertanol, blasticidin-S, Bordeaux mixture (Tribasic copper sulfate), boscalid/nicobifen, bromuconazole, bupirimate, buthiobate, carboxin, carpropamid, captafol, captan, carbendazim, chloroneb, chlorothalonil, chlozolinate, clotrimazole, copper oxychloride, copper salts such as copper sulfate and copper hydroxide, cyazofamid, cyflunamid, cymoxanil, cyproconazole, cyprodinil, dichlofluanid, diclocymet, diclomezine, dicloran, diethofencarb, difenoconazole, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinocap, discostrobin, dithianon, dodemorph, dodine, econazole, etaconazole, edifenphos, epoxiconazole, ethaboxam, ethirimol, ethridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid, fenfuram, fenhexamide, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferfurazoate, ferimzone, fluazinam, fludioxonil, flumetover, fluopicolide, fluoxastrobin, fluquinconazole, fluquinconazole, flusilazole, flusulfamide, flutolanil, flutriafol, folpet, fosetyl-aluminum, fuberidazole, furalaxyl, furametapyr, hexaconazole, hymexazole, guazatine, imazalil, imibenconazole, iminoctadine, iodicarb, ipconazole, iprobenfos, iprodione, iprovalicarb, isoconazole, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, mandipropamid, maneb, mapanipyrin, mefenoxam, mepronil, metalaxyl, metconazole, methasulfocarb, metiram, metominostrobin/fenominostrobin, mepanipyrim, metrafenone, miconazole, myclobutanil, neo-asozin (ferric methanearsonate), nuarimol, octhilinone, ofurace, orysastrobin, oxadixyl, oxolinic acid, oxpoconazole, oxycarboxin, paclobutrazol, penconazole, pencycuron, penthiopyrad, perfurazoate, phosphonic acid, phthalide, picobenzamid, picoxystrobin, polyoxin, probenazole, prochloraz, procymidone, propamocarb, propamocarb-hydrochloride, propiconazole, propineb, proquinazid, prothioconazole, pyraclostrobin, pryazophos, pyrifenox, pyrimethanil, pyrifenox, pyroInitrine, pyroquilon, quinconazole, quinoxyfen, quintozene, silthiofam, simeconazole, spiroxamine, streptomycin, sulfur, tebuconazole, techrazene, tecloftalam, tecnazene, tetraconazole, thiabendazole, thifluzamide, thiophanate, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolyfluanid, triadimefon, triadimenol, triarimol, triazoxide, tridemorph, trimoprhamide tricyclazole, trifloxystrobin, triforine, triticonazole, uniconazole, validamycin, vinclozolin, zineb, ziram, and zoxamide; nematocides such as aldicarb, imicyafos, oxamyl and fenamiphos; bactericides such as streptomycin; acaricides such as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad.

In certain instances, combinations of a compound of this invention with other biologically active (particularly invertebrate pest control) compounds or agents (i.e. active ingredients) can result in a greater-than-additive (i.e. synergistic) effect. Reducing the quantity of active ingredients released in the environment while ensuring effective pest control is always desirable. When synergism with invertebrate pest control active ingredients occurs at application rates giving agronomically satisfactory levels of invertebrate pest control, such combinations can be advantageous for reducing crop production cost and decreasing environmental load.

Compounds of this invention and compositions thereof can be applied to plants genetically transformed to express proteins toxic to invertebrate pests (such as Bacillus thuringiensis delta-endotoxins). Such an application may provide a broader spectrum of plant protection and be advantageous for resistance management. The effect of the exogenously applied compounds of this invention may be synergistic with the expressed toxin proteins.

General references for these agricultural protectants (i.e. insecticides, fungicides, nematocides, acaricides, herbicides and biological agents) include The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2003 and The BioPesticide Manual, 2^(nd) Edition, L. G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2001.

For embodiments where one or more of these various mixing partners are used, the weight ratio of these various mixing partners (in total) to a compound of Formula 1 is typically between about 1:3000 and about 3000:1. Of note are weight ratios between about 1:300 and about 300:1 (for example ratios between about 1:30 and about 30:1). One skilled in the art can easily determine through simple experimentation the biologically effective amounts of active ingredients necessary for the desired spectrum of biological activity. It will be evident that including these additional components can expand the spectrum of parasitic nematodes controlled beyond the spectrum controlled by a compound of Formula 1 alone.

Table A lists specific combinations of a compound of Formula 1 with other invertebrate pest control agents illustrative of the mixtures, compositions and methods of the present invention and includes additional embodiments of weight ratio ranges for application rates. The first column of Table A lists the specific invertebrate control agents (e.g., “Abamectin” in the first line). The second column of Table A lists the mode of action (if known) or chemical class of the invertebrate pest control agents. The third column of Table A lists embodiment(s) of ranges of weight ratios for rates at which the invertebrate pest control agent can be applied relative to a compound of Formula 1 (e.g., “50:1 to 1:50” of abamectin relative to a compound of Formula 1 by weight). Thus, for example, the first line of Table A specifically discloses the combination of a compound of Formula 1 with abamectin can be applied in a weight ratio between 50:1 to 1:50. The remaining lines of Table A are to be construed similarly.

TABLE A Invertebrate Pest Typical Control Agent Mode of Action or Chemical Class Weight Ratio Abamectin macrocyclic lactones 50:1 to 1:50 Acetamiprid neonicotinoids 150:1 to 1:200 Amitraz octopamine receptor ligands 200:1 to 1:100 Avermectin macrocyclic lactones 50:1 to 1:50 Azadirachtin ecdysone agonists 100:1 to 1:120 Beta-cyfluthrin sodium channel modulators 150:1 to 1:200 Bifenthrin sodium channel modulators 100:1 to 1:10  Buprofezin chitin synthesis inhibitors 500:1 to 1:50  Cartap nereistoxin analogs 100:1 to 1:200 Chlorantraniliprole ryanodine receptor ligands 100:1 to 1:120 Chlorfenapyr mitochondrial electron transport 300:1 to 1:200 inhibitors Chlorpyrifos cholinesterase inhibitors 500:1 to 1:200 Clothianidin neonicotinoids 100:1 to 1:400 Cyantraniliprole ryanodine receptor ligands 100:1 to 1:120 Cyfluthrin sodium channel modulators 150:1 to 1:200 Cyhalothrin sodium channel modulators 150:1 to 1:200 Cypermethrin sodium channel modulators 150:1 to 1:200 Cyromazine chitin synthesis inhibitors 400:1 to 1:50  Deltamethrin sodium channel modulators  50:1 to 1:400 Dieldrin cyclodiene insecticides 200:1 to 1:100 Dinotefuran neonicotinoids 150:1 to 1:200 Diofenolan molting inhibitor 150:1 to 1:200 Emamectin macrocyclic lactones 50:1 to 1:10 Endosulfan cyclodiene insecticides 200:1 to 1:100 Esfenvalerate sodium channel modulators 100:1 to 1:400 Ethiprole GABA-regulated chloride channel 200:1 to 1:100 blockers Fenothiocarb 150:1 to 1:200 Fenoxycarb juvenile hormone mimics 500:1 to 1:100 Fenvalerate sodium channel modulators 150:1 to 1:200 Fipronil GABA-regulated chloride channel 150:1 to 1:100 blockers Flonicamid 200:1 to 1:100 Flubendiamide ryanodine receptor ligands 100:1 to 1:120 Flufenoxuron chitin synthesis inhibitors 200:1 to 1:100 Hexaflumuron chitin synthesis inhibitors 300:1 to 1:50  Hydramethylnon mitochondrial electron transport 150:1 to 1:250 inhibitors Imidacloprid neonicotinoids 1000:1 to 1:1000 Indoxacarb sodium channel modulators 200:1 to 1:50  Lambda-cyhalothrin sodium channel modulators  50:1 to 1:250 Lufenuron chitin synthesis inhibitors 500:1 to 1:250 Metaflumizone 200:1 to 1:200 Methomyl cholinesterase inhibitors 500:1 to 1:100 Methoprene juvenile hormone mimics 500:1 to 1:100 Methoxyfenozide ecdysone agonists 50:1 to 1:50 Nitenpyram neonicotinoids 150:1 to 1:200 Nithiazine neonicotinoids 150:1 to 1:200 Novaluron chitin synthesis inhibitors 500:1 to 1:150 Oxamyl cholinesterase inhibitors 200:1 to 1:200 Pymetrozine 200:1 to 1:100 Pyrethrin sodium channel modulators 100:1 to 1:10  Pyridaben mitochondrial electron transport 200:1 to 1:100 inhibitors Pyridalyl 200:1 to 1:100 Pyriproxyfen juvenile hormone mimics 500:1 to 1:100 Ryanodine ryanodine receptor ligands 100:1 to 1:120 Spinetoram macrocyclic lactones 150:1 to 1:100 Spinosad macrocyclic lactones 500:1 to 1:10  Spirodiclofen lipid biosynthesis inhibitors 200:1 to 1:200 Spiromesifen lipid biosynthesis inhibitors 200:1 to 1:200 Tebufenozide ecdysone agonists 500:1 to 1:250 Thiacloprid neonicotinoids 100:1 to 1:200 Thiamethoxam neonicotinoids 1250:1 to 1:1000 Thiodicarb cholinesterase inhibitors 500:1 to 1:400 Thiosultap-sodium 150:1 to 1:100 Tralomethrin sodium channel modulators 150:1 to 1:200 Triazamate cholinesterase inhibitors 250:1 to 1:100 Triflumuron chitin synthesis inhibitors 200:1 to 1:100 Bacillus biological agents 50:1 to 1:10 thuringiensis Bacillus biological agents 50:1 to 1:10 thuringiensis delta-endotoxin NPV (e.g., Gemstar) biological agents 50:1 to 1:10

Of note is the composition of the present invention wherein the at least one additional biologically active compound or agent is selected from the invertebrate pest control agents listed in Table A above.

The weight ratios of a compound of Formula 1, an N-oxide, or a salt thereof, to the additional invertebrate pest control agent typically are between 1000:1 and 1:1000, with one embodiment being between 500:1 and 1:500, another embodiment being between 250:1 and 1:200 and another embodiment being between 100:1 and 1:50.

Listed below in Tables B1 to B14 are embodiments of specific compositions comprising a compound of Formula 1 (compound numbers (Cmpd. No.) refer to compounds in Index Tables A-D) and an additional invertebrate pest control agent.

TABLE B1 Mixture No. Cmpd. No. and Invertebrate Pest Control Agent B1-1 7 and Abamectin B1-2 7 and Acetamiprid B1-3 7 and Amitraz B1-4 7 and Avermectin B1-5 7 and Azadirachtin B1-5a 7 and Bensultap B1-6 7 and Beta-cyfluthrin B1-7 7 and Bifenthrin B1-8 7 and Buprofezin B1-9 7 and Cartap B1-10 7 and Chlorantraniliprole B1-11 7 and Chlorfenapyr B1-12 7 and Chlorpyrifos B1-13 7 and Clothianidin B1-14 7 and Cyantraniliprole B1-15 7 and Cyfluthrin B1-16 7 and Cyhalothrin B1-17 7 and Cypermethrin B1-18 7 and Cyromazine B1-19 7 and Deltamethrin B1-20 7 and Dieldrin B1-21 7 and Dinotefuran B1-22 7 and Diofenolan B1-23 7 and Emamectin B1-24 7 and Endosulfan B1-25 7 and Esfenvalerate B1-26 7 and Ethiprole B1-27 7 and Fenothiocarb B1-28 7 and Fenoxycarb B1-29 7 and Fenvalerate B1-30 7 and Fipronil B1-31 7 and Flonicamid B1-32 7 and Flubendiamide B1-33 7 and Flufenoxuron B1-34 7 and Hexaflumuron B1-35 7 and Hydramethylnon B1-36 7 and Imidacloprid B1-37 7 and Indoxacarb B1-38 7 and Lambda-cyhalothrin B1-39 7 and Lufenuron B1-40 7 and Metaflumizone B1-41 7 and Methomyl B1-42 7 and Methoprene B1-43 7 and Methoxyfenozide B1-44 7 and Nitenpyram B1-45 7 and Nithiazine B1-46 7 and Novaluron B1-47 7 and Oxamyl B1-48 7 and Phosmet B1-49 7 and Pymetrozine B1-50 7 and Pyrethrin B1-51 7 and Pyridaben B1-52 7 and Pyridalyl B1-53 7 and Pyriproxyfen B1-54 7 and Ryanodine B1-55 7 and Spinetoram B1-56 7 and Spinosad B1-57 7 and Spirodiclofen B1-58 7 and Spiromesifen B1-59 7 and Spirotetramat B1-60 7 and Tebufenozide B1-61 7 and Thiacloprid B1-62 7 and Thiamethoxam B1-63 7 and Thiodicarb B1-64 7 and Thiosultap-sodium B1-65 7 and Tolfenpyrad B1-66 7 and Tralomethrin B1-67 7 and Triazamate B1-68 7 and Triflumuron B1-69 7 and Bacillus thuringiensis B1-70 7 and Bacillus thuringiensis delta-endotoxin B1-71 7 and NPV (e.g., Gemstar)

Table B2

Table B2 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 19. For example, the first mixture in Table B2 is designated B2-1 and is a mixture of compound 19 and the additional invertebrate pest control agent abamectin.

Table B3

Table B3 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 30. For example, the first mixture in Table B3 is designated B3-1 and is a mixture of compound 30 and the additional invertebrate pest control agent abamectin.

Table B4

Table B4 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 68. For example, the first mixture in Table B4 is designated B4-1 and is a mixture of compound 20 and the additional invertebrate pest control agent abamectin.

Table B5

Table B5 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 170. For example, the first mixture in Table B5 is designated B5-1 and is a mixture of compound 170 and the additional invertebrate pest control agent abamectin.

Table B6

Table B6 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 179 For example, the first mixture in Table B6 is designated B6-1 and is a mixture of compound 179 and the additional invertebrate pest control agent abamectin.

Table B7

Table B7 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 180. For example, the first mixture in Table B7 is designated B7-1 and is a mixture of compound 180 and the additional invertebrate pest control agent abamectin.

Table B8

Table B8 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 356. For example, the first mixture in Table B8 is designated B8-1 and is a mixture of compound 356 and the additional invertebrate pest control agent abamectin.

Table B9

Table B9 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 357. For example, the first mixture in Table B9 is designated B9-1 and is a mixture of compound 357 and the additional invertebrate pest control agent abamectin.

Table B10

Table B10 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 382. For example, the first mixture in Table B10 is designated B10-1 and is a mixture of compound 382 and the additional invertebrate pest control agent abamectin.

Table B11

Table B11 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 413. For example, the first mixture in Table B11 is designated B11-1 and is a mixture of compound 413 and the additional invertebrate pest control agent abamectin.

Table B12

Table B12 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 465. For example, the first mixture in Table B12 is designated B12-1 and is a mixture of compound 465 and the additional invertebrate pest control agent abamectin.

Table B13

Table B13 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 474. For example, the first mixture in Table B13 is designated B13-1 and is a mixture of compound 474 and the additional invertebrate pest control agent abamectin.

Table B14

Table B14 is identical to Table B1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 394. For example, the first mixture in Table B14 is designated B14-1 and is a mixture of compound 394 and the additional invertebrate pest control agent abamectin.

The specific mixtures listed in Tables B1 to B14 typically combine a compound of Formula 1 with the other invertebrate pest agent in the ratios specified in Table A.

Listed below in Tables C1 to C14 are embodiments of specific compositions comprising a compound of Formula 1 (compound numbers (Cmpd. No.) refer to compounds in Index Tables A-D) and an additional fungicide.

TABLE C1 Mixture No. Cmpd. No. and Fungicide C1-1 7 and Probenazole C1-2 7 and Tiadinil C1-3 7 and Isotianil C1-4 7 and Pyroquilon C1-5 7 and Metominostrobin C1-6 7 and Flutolanil C1-7 7 and Validamycin C1-8 7 and Furametpyr C1-9 7 and Pencycuron C1-10 7 and Simeconazole C1-11 7 and Orysastrobin C1-12 7 and Trifloxystrobin C1-13 7 and Isoprothiolane C1-14 7 and Azoxystrobin C1-15 7 and Tricyclazole C1-16 7 and Hexaconazole C1-17 7 and Difenoconazole C1-18 7 and Cyproconazole C1-19 7 and Propiconazole C1-20 7 and Fenoxanil C1-21 7 and Ferimzone C1-22 7 and Fthalide C1-23 7 and Kasugamycin C1-24 7 and Picoxystrobin C1-25 7 and Penthiopyrad C1-26 7 and Famoxadone C1-27 7 and Cymoxanil C1-28 7 and Proquinazid C1-29 7 and Flusilazole C1-30 7 and Mancozeb C1-31 7 and Copper hydroxide C1-32 7 and (a) (a) 1-[4-[4-[5-(2,6-difluorophenyl)-4,5-dihydro-3-isoxazolyl]-2-thiazolyl]-2-piperidinyl]-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone

Table C2

Table C2 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 19. For example, the first mixture in Table C2 is designated C2-1 and is a mixture of compound 19 and the additional fungicide probenazole.

Table C3

Table C3 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 30. For example, the first mixture in Table C3 is designated C3-1 and is a mixture of compound 30 and the additional fungicide probenazole.

Table C4

Table C4 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 68. For example, the first mixture in Table C4 is designated C4-1 and is a mixture of compound 68 and the additional fungicide probenazole.

Table C5

Table C5 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 170. For example, the first mixture in Table C5 is designated C5-1 and is a mixture of compound 170 and the additional fungicide probenazole.

Table C6

Table C6 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 179. For example, the first mixture in Table C6 is designated C6-1 and is a mixture of compound 179 and the additional fungicide probenazole.

Table C7

Table C7 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 180. For example, the first mixture in Table C7 is designated C7-1 and is a mixture of compound 180 and the additional fungicide probenazole.

Table C8

Table C8 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 356. For example, the first mixture in Table C8 is designated C8-1 and is a mixture of compound 356 and the additional fungicide probenazole.

Table C9

Table C9 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 357. For example, the first mixture in Table C9 is designated C9-1 and is a mixture of compound 357 and the additional fungicide probenazole.

Table C10

Table C10 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 382. For example, the first mixture in Table C10 is designated C10-1 and is a mixture of compound 382 and the additional fungicide probenazole.

Table C11

Table C11 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 413. For example, the first mixture in Table C11 is designated C11-1 and is a mixture of compound 413 and the additional fungicide probenazole.

Table C12

Table C12 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 465. For example, the first mixture in Table C12 is designated C12-1 and is a mixture of compound 465 and the additional fungicide probenazole.

Table C13

Table C13 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 474. For example, the first mixture in Table C13 is designated C13-1 and is a mixture of compound 474 and the additional fungicide probenazole.

Table C14

Table C14 is identical to Table C1, except that each reference to compound 7 in the column headed “Cmpd. No.” is replaced by a reference to compound 394. For example, the first mixture in Table C14 is designated C14-1 and is a mixture of compound 394 and the additional fungicide probenazole.

Parasitic nematodes are controlled in agronomic and nonagronomic applications by applying one or more compounds of this invention, typically in the form of a composition, in a biologically effective amount, to the environment of the pests, including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled.

Thus the present invention comprises a method for controlling a parasitic nematode in agronomic and/or nonagronomic applications, comprising contacting the parasitic nematode or its environment with a biologically effective amount of one or more of the compounds of the invention, or with a composition comprising at least one such compound or a composition comprising at least one such compound and at least one additional biologically active compound or agent. Examples of suitable compositions comprising a compound of the invention and at least one additional biologically active compound or agent include granular compositions wherein the additional active compound is present on the same granule as the compound of the invention or on granules separate from those of the compound of the invention.

To achieve contact with a compound or composition of the invention to protect a field crop from parasitic nematodes, the compound or composition is typically applied to the seed of the crop before planting, to the foliage (e.g., leaves, stems, flowers, fruits) of crop plants, or to the soil or other growth medium before or after the crop is planted.

One embodiment of a method of contact is by spraying. Alternatively, a granular composition comprising a compound of the invention can be applied to the plant foliage or the soil. Compounds of this invention can also be effectively delivered through plant uptake by contacting the plant with a composition comprising a compound of this invention applied as a soil drench of a liquid formulation, a granular formulation to the soil, a nursery box treatment or a dip of transplants. Of note is a composition of the present invention in the form of a soil drench liquid formulation. Also of note is a method for controlling a parasitic nematode comprising contacting the parasitic nematode or its environment with a biologically effective amount of a compound of the present invention or with a composition comprising a biologically effective amount of a compound of the present invention. Of further note is this method wherein the environment is soil and the composition is applied to the soil as a soil drench formulation. Of further note is that compounds of this invention are also effective by localized application to the locus of infestation. Other methods of contact include application of a compound or a composition of the invention by direct and residual sprays, aerial sprays, gels, seed coatings, microencapsulations, systemic uptake, baits, ear tags, boluses, foggers, fumigants, aerosols, dusts and many others. One embodiment of a method of contact involves a dimensionally stable fertilizer granule, stick or tablet comprising a compound or composition of the invention. The compounds of this invention can also be impregnated into materials for fabricating invertebrate control devices (e.g., insect netting).

Compounds of this invention are also useful in seed treatments for protecting seeds from parasitic nematodes. In the context of the present disclosure and claims, treating a seed means contacting the seed with a biologically effective amount of a compound of this invention, which is typically formulated as a composition of the invention. This seed treatment protects the seed from invertebrate soil pests and generally can also protect roots and other plant parts in contact with the soil of the seedling developing from the germinating seed. The seed treatment may also provide protection of foliage by translocation of the compound of this invention or a second active ingredient within the developing plant. Seed treatments can be applied to all types of seeds, including those from which plants genetically transformed to express specialized traits will germinate. Representative examples of genetically transformed plants include those expressing proteins toxic to parasitic nematodes, such as Bacillus thuringiensis toxin or those expressing herbicide resistance such as glyphosate acetyltransferase, which provides resistance to glyphosate.

One method of seed treatment is by spraying or dusting the seed with a compound of the invention (i.e. as a formulated composition) before sowing the seeds. Compositions formulated for seed treatment generally comprise a film former or adhesive agent. Therefore typically a seed coating composition of the present invention comprises a biologically effective amount of a compound of Formula 1, an N-oxide, or salt thereof, and a film former or adhesive agent. Seed can be coated by spraying a flowable suspension concentrate directly into a tumbling bed of seeds and then drying the seeds. Alternatively, other formulation types such as wetted powders, solutions, suspo-emulsions, emulsifiable concentrates and emulsions in water can be sprayed on the seed. This process is particularly useful for applying film coatings on seeds. Various coating machines and processes are available to one skilled in the art. Suitable processes include those listed in P. Kosters et al., Seed Treatment Progress and Prospects, 1994 BCPC Mongraph No. 57, and references listed therein.

The treated seed typically comprises a compound of the present invention in an amount from about 0.1 g to 1 kg per 100 kg of seed (i.e. from about 0.0001 to 1% by weight of the seed before treatment). A flowable suspension formulated for seed treatment typically comprises from about 0.5 to about 70% of the active ingredient, from about 0.5 to about 30% of a film-forming adhesive, from about 0.5 to about 20% of a dispersing agent, from 0 to about 5% of a thickener, from 0 to about 5% of a pigment and/or dye, from 0 to about 2% of an antifoaming agent, from 0 to about 1% of a preservative, and from 0 to about 75% of a volatile liquid diluent.

For agronomic applications, the rate of application required for effective control (i.e. “biologically effective amount”) will depend on such factors as the species of nematode to be controlled, the nematode's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredients per hectare are sufficient to control nematodes in agronomic ecosystems, but as little as 0.0001 kg/hectare may be sufficient or as much as 8 kg/hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required. One skilled in the art can easily determine the biologically effective amount necessary for the desired level of parasitic nematode control.

The compounds of this invention prepared by the methods described herein are shown in Index Tables A-E. For mass spectral data, the numerical value reported in the column “AP⁺ (M+1)”, is the molecular weight of the observed molecular ion formed by addition of H⁺ (molecular weight of 1) to the molecule having the greatest isotopic abundance (i.e. M); the numerical value reported in the column “AP⁻ (M−1)”, is the molecular weight of the observed molecular ion formed by loss of H⁺ (molecular weight of 1) from the molecule having the greatest isotopic abundance (i.e. M). The presence of molecular ions containing one or more higher atomic weight isotopes of lower abundance (e.g., ³⁷Cl, ⁸¹Br) is not reported. The reported M+1 and M−1 peaks were observed by mass spectrometry using atmospheric pressure chemical ionization (AP⁺).

The following abbreviations are used in the Index Tables which follow: Cmpd means Compound. The variables “R” and “(R¹)_(n)” represent one or a combination of substituents as listed in the Index Tables. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which Synthesis Example the compound is prepared.

INDEX TABLE A

AP+ AP− Cmpd R ** m.p. (° C.) (M + 1) (M − 1) 1 2-methoxy, 5-chloro 248-250 2 2-methoxy, 5-methyl  250 3 2-methoxy, 5-cyano  250 4 2-difluoromethyl, 5-fluoro 231-232 5 2-methoxy, 5-trifluoromethyl  250 6 2-difluoromethyl, 5-methoxy 196-197 7 2-chloro, 5-methoxy 211-212 (Ex. 1) 8 2-difluoromethoxy, 5-methyl 216-217 9 2-difluoromethyl, 5-chloro 229-230 10 2-chloro, 5-cyano  250 11 2-methyl, 5-bromo 216-217 12 2-methyl, 5-CO₂CH₃ 206-207 13 2-methyl, 5-isopropyl 226-227 14 2-methoxy, 5-CO₂CH₃ >250 15 2-methyl, 5-S(O)₂CH₃ 248-249 16 2-SCH₂CH₃, 5-chloro 229-230 17 2-nitro, 5-chloro >250 18 2-SCH₃, 5-chloro >250 19 2-chloro, 5-C(O)CH₃ 244-245 20 2-trifluoromethyl, 5-chloro 219-220 21 2-SCH₃, 5-methoxy 236-237 22 2-chloro, 5-OCH₂Ph >250 23 2-chloro-5-S(O)₂CH₃ 241-242 24 2,4-dichloro, 5-CO₂CH₃ 164-165 25 2-chloro, 4-cyano 224-225 26 2-iodo 243-244 27 2-iodo, 4-trifluoromethyl 229-230 28 2-chloro, 5-CO₂CH₃ 245-246 29 2,4,6-trifluoro 222-223 30 2,5-dimethyl, 4-cyano 228-229 (Ex. 2) 31 2-difluoromethyl 193-194 32 2-methyl, 3-chloro 196-197 33 4-CO₂CH₃ 243-244 34 2-NHC(O)CH₃ 242-243 35 2-SCH₃, 3-chloro 200-201 36 2-methyl, 6-difluoromethoxy 237-238 37 2-difluoromethoxy, 4-methyl 182-183 38 2-methyl, 4-difluoromethoxy 197-198 39 3-chloro, 4-nitro 198-199 40 3-nitro, 4-chloro 196-197 41 2-chloro, 6-CH₂OCH₃ 207-208 42 4-S(O)₂CH₃ >250 43 2-(2-pyridinyl) >250 44 2-phenyl 251-252 45 3-nitro, 4-methoxy 245-246 46 2-methoxy, 3-propyl 168-169 47 2-OC(CH₃)₃ 208-209 48 2-CO₂CH₃, 4-methyl >250 49 2-CH₂CO₂CH₃ 162-163 50 2-(2-(1,3,4-oxadiazinyl)) >250 51 2-(1-(1,3,4-triazinyl)) >250 52 2-(5-isoxazolyl) >250 53 2-(2-oxazolyl) >250 54 2-(4-isoxazolyl) 231-232 55 2-(1-imidazolyl) 157-158 56 2-(1-pyrazolyl) >250 57 2-cyano, 3-chloro 215-216 58 2-nitro, 3-methyl 241-242 59 2-nitro, 5-methyl 249-250 60 2-(CH(CH₃)OCH₃ 224-225 61 2-ethoxy, 3-methyl 157-158 62 2-methoxy, 3-chloro 191-192 63 2,5-dimethyl, 4-chloro 213-214 64 2-fluoro, 6-CH₂OCH₃ 182-183 65 2-isopropyl, 4-cyano, 5-methyl 216-217 66 2,5-dimethyl, 4-bromo 224-225 67 2,5-dimethyl, 4-isopropyl 193-194 68 2-nitro, 5-methoxy 233-234 69 3-methyl, 4-cyano 231-232 70 2,5-diisopropyl, 4-cyano 209-210 71 2,5-diethyl, 4-cyano 237-238 72 2,5-dipropyl, 4-cyano 181-182 73 2,5-diethyl, 4-fluoro 187-188 74 2,5-diisopropyl, 4-nitro 198-199 75 2,5-diisopropyl, 4-methoxy 141-142 76 2,6-dimethyl >250 77 3-isopropyl, 4-methoxy 182-183 78 2,5-diisopropyl, 4-methyl 185-186 79 2-cyano, 3-fluoro 227-228 80 2-S(O)₂N(CH₃)₂, 3-methoxy 157-158 81 2-ethyl 190-191 82 3-chloro, 4-methoxy 204-205 83 2,3-dimethyl, 5-nitro >250 85 2-isopropyl 190-191 86 2-methyl 193-194 87 2-iodo 149-150 88 2-S(O)CH₃, 5-methoxy 147-149 89 2-fluoro, 4,5-dimethoxy 159-160 90 2-methyl, 4,5-dimethoxy 196-197 91 2,3,4,5-tetramethyl >250 92 2,3,4,6-tetramethyl 220-221 93 2,4,5-trimethyl 208-209 94 — 404 402 95 4-methoxy 432 96 4-methyl 418 416 97 4-chloro 438 436 98 3-chloro 438 436 99 4-cyano 427 100 3,5-dichloro 472 470 101 2,5-dichloro 470 102 2-methyl, 4-fluoro 245-250 103 2-methyl, 5-fluoro 436 434 104 2-trifluoromethyl 472 470 105 2-bromo 482 106 3,4-dichloro 472 470 107 2,4-dichloro 472 470 108 2-fluoro * 109 2-methyl 418 416 110 2,3,4-trichloro 504 111 2-methyl, 5-chloro 452 450 112 2-chloro, 5-nitro 483 113 2,4,5-trichloro 504 114 2,3-dichloro 472 470 115 2-methoxy 434 432 116 2-methyl, 5-nitro 463 461 117 2,6-difluoro 440 438 118 2-cyclopropyl 444 442 119 2-trifluoromethoxy 488 486 120 2,4,6-trimethyl 444 121 2-cyano 429 427 122 2-CO₂CH₃ 462 460 123 2-nitro 449 124 2-S(O)₂CH₃ 482 480 125 OCH₂C≡CH 458 456 126 2-trifluoromethoxy, 4-bromo 566 564 127 2,5-dimethoxy 464 462 128 2-SCH₂CH₂CH₃ 476 129 2,3,4,5,6-pentafluoro 494 492 130 2-chloro, 4-methyl 452 450 131 2,4-difluoro 440 438 132 2,5-difluoro 440 438 133 2-fluoro, 5-chloro 456 454 134 3-fluoro 422 420 135 3,5-difluoro 440 438 136 2-fluoro, 4-chloro 456 454 137 2-fluoro, 5-methyl 204-205 138 2-chloro, 4-trifluoromethyl 506 504 139 2,5-dimethyl 432 430 140 3 -methoxy * 141 3-nitro 449 447 142 2-(1-methyltetrazolyl) 486 484 143 2-fluoro, 5-trifluoromethyl 490 488 144 3-cyano 429 427 145 3 -trifluoromethyl 472 470 146 3-bromo 482 480 147 2,6-dichloro, 4-trifluoromethyl 542 540 148 3-amino 417 149 2-bromo, 4-fluoro 502 500 150 2-bromo, 4-trifluoromethyl 550 151 2-methyl, 5-difluoromethoxy 225-226 319 2-bromo, 5-trifluoromethyl * 329 2-methyl, 5-trifluoromethyl 257-258 330 2,4-dichloro, 5-methyl 234-235 331 2-methyl, 4-bromo, 5-methoxy 228-229 332 2-methyl, 4- cyano, 5-methoxy 160-162 333 2-methyl, 4,5-dichloro 160-161 334 2-acetyl 222-223 335 4-nitro >250 336 2-iodo, 4-methoxy 204-205 337 2-trifluoromethoxy, 5-chloro 212-213 338 2-dimethylamino, 5-nitro 220-221 339 3,5-dicarbomethoxy 231-232 340 3 ,5-di(trifluoromethyl) >250 341 2,5-dibromo, 4-isopropyl 143-144 342 2-methyl, 4-bromo 207-208 343 2-methyl, 5-methoxy 206-207 344 2,5-difluoro, 4-bromo 208-209 345 2-nitro, 4-isopropyl, 5-bromo 210-211 346 2,6-dibromo, 4-methyl 198-199 347 2-methyl, 4-chloro 209-210 348 3 -dimethylamino 126-127 349 4-fluoro 242-243 350 4-(CF₂CF₂H) 194-195 351 2-iodo, 3-nitro 246-247 352 2-fluoro, 3-chloro 239-240 353 2-bromo, 3-methyl 206-207 354 2,5-dicarbomethoxy 234-235 355 2,5-diethyl, 4-bromo 184-185 356 2-chloro, 5-methyl >250 357 2-bromo, 5-methyl 251-252 358 2-SO₂N(CH₃)₂, 5-methylthio 225-226 359 2-chloro, 5-ethoxy 255-256 360 2,5-dichloro, 4-nitro 225-226 361 2,5-dimethyl, 4-methoxy 233-234 362 2-C(CH₃)₃ 175-176 363 2-(CH═NOCH₃) 200-201 364 2,5-dimethyl, 4-iodo 219-220 365 2,5-dimethyl, 201-202 4-(C≡CSi(CH₃)₃) 366 2,5-dimethyl, 4-(C≡CH) 171-172 367 2-chloro, 5-isopropoxy 217-218 368 3-SO₂N(CH₃)₂ 219-220 369 2,5-di(C(O)N(CH₃)₂) 198-199 370 2,5-di(SO₂N(CH₃)₂) 171-172 371 2-chloro, 5-OCH₂CF₃ >250 372 2,4-dichloro, 5-OCH₂C≡CH 202-203 373 2-chloro, 5-amino 195-196 374 2-chloro, 5-hydroxy 139-140 375 2-chloro, 5-NHC(O)CH₃ 206-207 376 2-chloro, 5-OCH₂CH═CH₂ 251-252 377 2-chloro, 5-OCH₂C≡CH 217-218 378 2-chloro, 5-NHC(O)OCH₃ 255-256 379 2-chloro, 5-bromo >250 380 2-chloro, 5-(C≡CSi(CH₃)₃) >250 381 2-chloro, 5-(C≡CH) 238-240 382 2-chloro, 5-ethyl 214-215 (Ex. 3) 383 2-chloro, 5-dimethylamino >250 384 2-methyl, 5-dimethylamino >250 385 2-chloro, 4-bromo, 5-methoxy 224-225 386 2-chloro, 4-cyano, 5-methoxy >250 387 2-chloro, 4-bromo, 5-methyl 210-211 388 2-chloro, 4-cyano, 5-methyl 229-230 389 2-chloro, 5-methylthio 255-256 390 3-NHC(O)CH₂CH₂CH₃ 167-168 391 NHC(O)NHCH₃ 188-189 392 2-chloro, 5-OC(O)CH₃ 178-179 393 3 -NHC(O)(4-fluorophenyl) 201-202 394 2-methyl, 5-acetyl 222-223 395 2-bromo, 5-propyl 213-214 396 2-propyl, 5-bromo 244-245 397 2-bromo, 5-isopropyl 204-205 398 2-isopropyl, 5-bromo 129-130 399 2-ethyl, 5-chloro 219-220 480 2-chloro, 5-trifluoromethoxy 217-218 * See Index Table E for ¹H NMR data. ** “—” denotes R is H (i.e. the phenyl ring is unsubstituted)

INDEX TABLE B

R² is H AP+ AP− Cmpd (R¹)_(n) Q m.p. (° C.) (M + 1) (M − 1) 152 3-CF₃, 5-Cl 3-chloro-2-pyridinyl 196-197 153 3-CF₃, 5-Cl 6-chloro-2-pyridinyl 236-237 154 3-CF₃, 5-Cl 3-bromo-2-pyridinyl 192-193 155 3-CF₃, 5-Cl 3-CF₃-6-OCH₃-2-pyridinyl 211-212 156 3-CF₃, 5-Cl 3-CO₂CH₃-6-CF₃-2-pyridinyl 212-213 157 3-CF₃, 5-Cl 3-OCH₂CF₃-6-CF₃-2-pyridinyl 244-245 158 3-CF₃, 5-Cl 3-iodo-6-chloro-2-pyridinyl 241-242 159 3-CF₃, 5-Cl 3-CF₃-2-pyridinyl 176-177 160 3-CF₃, 5-Cl 6-CF₃-2-pyridinyl 236-237 161 3-CF₃, 5-Cl 3-C(O)N(CH₃)₂-6-CF₃-2-pyridinyl 152-153 162 3-CF₃, 5-Cl 4-chloro-3-pyridinyl 196-197 163 3-CF₃, 5-Cl 2-chloro-3-pyridinyl 194-195 164 3-CF₃, 5-Cl 2-SCH₂CH₃-3-pyridinyl 255-256 165 3-CF₃, 5-Cl 2-OCH₂CH₃-3-pyridinyl 192-193 166 3-CF₃, 5-Cl 4-CF₃-2-pyridinyl 229-230 167 3-CF₃, 5-Cl 2-chloro-5-thiazolyl 208-209 168 3-CF₃, 5-Cl 2-chloro-5-thienyl 216-217 169 3-CF₃, 5-Cl

252-253 170 3-CF₃, 5-Cl 1-methyl-3-chloro-4-pyrazolyl 202-203 171 3-CF₃, 5-Cl 1-methyl-4-chloro-3-pyrazolyl >250 172 3-CF₃, 5-Cl 1-methyl-5-chloro-4-pyrazolyl >250 173 3-CF₃, 5-Cl

190-191 174 3-CF₃, 5-Cl 1-methyl-5-ethyl-4-pyrazolyl 212-214 175 3-CF₃, 5-Cl 1,3,5-trimethyl-4-pyrazolyl >250 176 3-CF₃, 5-Cl 2,4-dimethyl-5-thiazolyl 202-203 177 3-CF₃, 5-Cl 2-cyano-3-thienyl 251-252 178 3-CF₃, 5-Cl 2-methyl-1,3,4-thiadiazol-5-yl 204-205 179 3-CF₃, 5-Cl 3-methyl-2-thienyl 218-219 180 3-CF₃, 5-Cl 4-methyl-2-thienyl 195-196 181 3-CF₃, 5-Cl 1-ethyl-5-pyrazolyl  169 182 3-CF₃, 5-Cl 1,5-dimethyl-4-pyrazolyl 242-243 183 3-CF₃, 5-Cl 4-methyl-2-pyridinyl 212-213 184 3-CF₃, 5-Cl 1-methyl-5-pyrazolyl 176-177 185 3-CF₃, 5-Cl 1-methyl-4-pyrazolyl 240-241 186 3-CF₃, 5-Cl 2-furanyl 216-217 187 3-CF₃, 5-Cl

>250 188 3-CF₃, 5-Cl

210-211 189 3-CF₃, 5-Cl

223-224 190 3-CF₃, 5-Cl 3-nitro-2-thienyl 233-234 191 3-CF₃, 5-Cl 1-methyl-4-SCH₃-5-pyrazolyl 178-179 192 3-CF₃, 5-Cl 1-methyl-2SCH₃-3-pyrrolyl 226-227 193 3-CF₃, 5-Cl

233-235 194 3-CF₃, 5-Cl

238-240 195 3-CF₃, 5-Cl 2-(2-thienyl)phenyl 243-244 196 3-CF₃, 5-Cl 1-methyl-5-SO₂CH₃-4-pyrazolyl >250 197 3-CF₃, 5-Cl 2-(3-methyl-1,2,4-oxadiazol-5-yl) 252-253 198 3-CF₃, 5-Cl 2-cyano-3-benzothiazolyl 205-206 199 3-CF₃, 5-Cl

243-244 200 3-CF₃, 5-Cl

222-223 201 3-CF₃, 5-Cl

206-207 202 3-CF₃, 5-Cl

236-237 203 3-CF₃, 5-Cl 2-(3-methyl-5-isoxazolyl)phenyl 234-235 204 3-CF₃, 5-Cl 2-(1-methyl-4-pyrazolyl)phenyl 211-212 205 3-CF₃, 5-Cl 1-benzyl-4-imidazolyl >250 206 3-CF₃, 5-Cl 1-benzyl-4-pyrazolyl 226-227 208 3-CF₃, 5-Cl 2-methyl-4-CO₂CH₃-5-oxazolyl 171-172 209 3-CF₃, 5-Cl 1-methyl-4-CO₂CH₂CH₃-3-pyrazolyl >250 210 3-CF₃, 5-Cl 1,3-dimethyl-5-CO₂CH₃-4-pyrazolyl 232-233 211 3-CF₃, 5-Cl 3-CO₂CH(CH₃)₂-2-furanyl 173-174 212 3-CF₃, 5-Cl 1-methyl-4-CON(CH₃)₂-5-pyrazolyl 254-255 213 3-CF₃, 5-Cl 1-cyano-3-naphthalenyl 226-227 214 3-CF₃, 5-Cl 1-cyano-4-naphthalenyl 203-204 215 3-CF₃, 5-Cl 1-methyl-5-CON(CH₃)₂-4-pyrrolyl 178-179 216 3-CF₃, 5-Cl 1-methyl-3-(5-oxazolyl)-4-pyrazolyl 252-253 217 3-CF₃, 5-Cl 3-methyl-2-benzothienyl 229-230 218 3-CF₃, 5-Cl

>250 219 3-CF₃, 5-Cl 3-SO₂CH₃-2-furanyl 243-244 220 3-CF₃, 5-Cl 2-(1,2,4-triazol-1-yl)-3-pyridinyl >250 221 3-CF₃, 5-Cl 3-CON(CH₃)₂-2-thienyl 219-220 222 3-CF₃, 5-Cl

246-247 223 3-CF₃, 5-Cl 1-phenyl-2-imidazolyl 211-212 224 3-CF₃, 5-Cl 2-CON(CH₃)₂-3-furanyl 200-201 225 3-CF₃, 5-Cl 3-CO₂CH₃-1,2,5-thiadiazol-4-yl 195-196 226 3-CF₃, 5-Cl 4-CO₂CH₃-5-thiazolyl 220-221 227 3-CF₃, 5-Cl 2-methyl-1-naphthalenyl 219-220 228 3-CF₃, 5-Cl 2-CO₂CH₃-3-thienyl 224-225 229 3-Cl phenyl 334 230 3-Cl 4-methylphenyl 350 348 231 3-Cl 4-chlorophenyl 368 232 3-Cl 4-methoxyphenyl 366 364 233 3-Cl 4-cyanophenyl 359 234 3-Cl 3-chlorophenyl 368 237 3-Cl 3,5-dichlorophenyl 402 238 3-Cl 2,5-dichlorophenyl 230-232 239 3-Cl 2-methyl-4-fluorophenyl 265-270 240 3-Cl 2-methyl-5-fluorophenyl 366 241 3-CF₃, 5-Cl 2-pyridinyl 403 242 3-Cl, 5-Cl 2-chlorophenyl 404 402 243 3-Cl, 5-Cl 2,5-dichlorophenyl 438 436 244 3-CF₃, 5-Cl 3-methyl-2-pyridinyl 419 417 245 3-CF₃, 5-Cl 2-thienyl 410 408 246 3-Cl, 5-Cl 2-chloro-5-(trifluoromethyl)phenyl 472 470 247 3-Cl, 5-Cl 2-chloro-6-methylphenyl 418 416 248 3-CF₃ 2-chlorophenyl 404 402 249 3-Cl 2-chlorophenyl 368 250 5-CF₃ 2-chlorophenyl 404 402 251 3-CF₃, 5-Cl 1,3-dimethyl-4-pyrazolyl * 252 3-Br, 5-Br 2-chlorophenyl 492 490 253 3-I 2-chlorophenyl 462 460 254 5-CN 2-chlorophenyl 359 255 3-CF₃, 5-Cl 3-chloro-2-thienyl 442 256 3-CF₃, 5-Cl 2,5-dichloro-3-thienyl 478 476 257 3-Br 2-chlorophenyl 414 412 258 3-CF₃, 5-Cl 3-bromo-2-thienyl 490 488 259 — 2-chlorophenyl 336 334 260 3-CF₃, 5-Cl 2-CON(CH₃)₂-3-thienyl 479 261 3-CF₃, 5-Cl

496 494 262 3-CF₃, 5-Cl 5-imadazolyl 394 392 263 3-CF₃, 5-Cl 4,5-dichloro-2-thienyl 476 264 3-CF₃, 5-Cl 5-bromo-6-chloro-3-pyridinyl 515 265 3-CF₃, 5-Cl 4,5-dibromo-2-thienyl 564 266 3-CH₃, 5-Cl 3-methoxyphenyl 380 378 267 3-CH₃, 5-Cl 2,5-dimethylphenyl 378 376 268 3-CF₃, 5-Cl 4-bromo-3-thienyl 488 269 3-CH₃, 5-Cl 2-chlorophenyl 384 382 270 3-CH₃, 5-Cl 2-thienyl 356 354 271 3-CH₃, 5-Cl 3,5-dimethyl-4-isoxazolyl 369 367 272 3-CF₃, 5-Cl 3-thienyl 410 408 273 3-CH₃, 5-Cl 2-chloro-5-(trifluoromethyl)phenyl 452 274 3-CF₃, 5-Cl 5-chloro-1,3-dimethyl-4-pyrazolyl 456 454 275 3-CF₃, 5-Cl 1-methyl-4-imidazolyl 408 406 276 3-CF₃ 3,5-dimethyl-4-isoxazolyl 389 387 277 3-Br, 5-Br 3,5-dimethyl-4-isoxazolyl 477 475 278 3-Br, 5-Br 2-chloro-5-(trifluoromethyl)phenyl * 279 3-Br, 5-Br 2,5-dimethylphenyl * 280 3-Br, 5-Br 2-thienyl * 281 3-Br, 5-Br 3-methoxyphenyl * 282 3-CN 2-fluorophenyl 345 343 283 3-CN 2-thienyl 331 284 3-CN 2-chloro-5-(trifluoromethyl)phenyl * 285 3-CN 2,5-dimethylphenyl 353 286 3-CN 2-chlorophenyl 359 287 3-CF₃, 5-CF₃ 2-fluorophenyl 456 454 288 3-CF₃, 5-CF₃ 2-chloro-5-(trifluoromethyl)phenyl 540 289 3-C(O)NH₂ 2-fluorophenyl * 290 5-Cl 2-thienyl 340 291 3-CF₃ 2-thienyl 328 292 3-CF₃ 2,5-dimethylphenyl 398 396 293 5-Cl 2-chloro-5-(trifluoromethyl)phenyl 438 294 5-Cl 2-chlorophenyl 370 368 295 5-Cl 2-fluorophenyl 354 352 296 5-Cl 2,5-dimethylphenyl 364 362 297 3-CF₃ 2,5-dibromophenyl 560 298 3-CF₃ 2-fluorophenyl 388 386 299 3-CF₃ 2-methylphenyl 384 382 300 3-CF₃ 2-chloro-4-(trifluoromethyl)phenyl 472 470 301 3-CF₃ 2-chloro-4-fluorophenyl 420 302 2-CF₃ 2,5-dimethylphenyl 398 396 303 2-CF₃ 2-chlorophenyl 404 402 304 2-CF₃ 2-thienyl 376 324 305 2-CF₃ 3-methoxyphenyl 400 398 306 2-CF₃ 2-fluorophenyl 388 386 307 4-CF₃ 2,5-dimethylphenyl 398 396 308 4-CF₃ 2-chlorophenyl 404 402 309 4-CF₃ 2-thienyl 376 374 310 4-CF₃ 3-methoxyphenyl 400 398 311 4-CF₃ 2-fluorophenyl 388 386 312 2-CF₃ 2-chloro-5-(trifluoromethyl)phenyl 472 470 313 4-CF₃ 2-chloro-5-(trifluoromethyl)phenyl 472 470 314 3-CF₃, 5-Br 2-chloro-5-(trifluoromethyl)phenyl 550 548 315 3-CF₃, 5-Br 2-bromo-5-(trifluoromethyl)phenyl * 316 3-CF₃, 5-Br 2-fluorophenyl 466 465 400 3-CF₃, 5-Cl 2,5-dichloro-4-bromo-3-thienyl 245-246 401 3-CF₃, 5-Br 2-chlorophenyl 188-193 403 3-CF₃, 5-Br 2,5-dimethylphenyl >250 404 3-CF₃, 5-Br 3,5-dimethyl-4-isoxazolyl 224-225 405 3-CF₃, 5-Br 4-cyano-2,5-dimethylphenyl 193-194 406 3-CF₃, 5-F 2,5-dimethylphenyl 181-182 407 3-CF₃, 5-F 2-chloro-5-(trifluoromethyl)phenyl 186-187 408 3-CF₃, 5-F 4-chloro-2,5-dimethylphenyl 185-186 409 3-CF₃, 5-F 3,5-dimethyl-4-isoxazolyl 176-177 410 3-CF₃, 5-Br 4-chloro-2,5-dimethylphenyl 190-191 411 3-CF₃, 5-Br 4,5-dimethoxy-2-methylphenyl 110-111 412 3-CF₃, 5-F 4,5-dimethoxy-2-methylphenyl 100-101 413 (Ex. 6) 3-CF₃, 5-Br 2-chloro-5-methoxyphenyl 191-192 414 3-CF₃, 5-F 2-chloro-5-methoxyphenyl 193-194 415 3-CF₃, 5-F 4-cyano-2,5-dimethylphenyl 206-207 416 3-CF₃, 5-OCH₂CH₃ 2,5-dimethylphenyl 195-196 417 3-CF₃, 5-OCH₂CH₃ 2-chloro-5-(trifluoromethyl)phenyl 189-190 418 3-CF₃, 5-OCH₂CH₃ 4-chloro-2,5-dimethylphenyl 194-195 419 3-CF₃, 5-OCH₂CH₃ 3,5-dimethyl-4-isoxazolyl 196-197 420 3-CF₃ 5-acetyl-2-chlorophenyl 217-218 421 3-CF₃ 4,5-dimethoxy-2-methylphenyl 164-165 422 — 2-chloro-5-methoxyphenyl >250 423 — 4-cyano-2,5-dimethylphenyl >250 424 3-CF₃ 2-chloro-5-(trifluoromethyl)phenyl >250 425 — 3,5-dimethyl-4-isoxazolyl 239-240 426 3-CF₃, 5-Cl 6-chloro-5-(trifluoromethyl)-2-pyridinyl 236-237 427 3-CF₃ 4-cyano-5-methoxy-2-methylphenyl 227-228 432 — 2-chloro-5-(trifluoromethyl)phenyl >250 433 3-CF₃, 5-Cl 3-methyl-6-methylamino-2-pyridinyl >250 434 3-CF₃, 5-Cl 3-chloro-6-methylamino-2-pyridinyl 190-191 435 3-CF₃, 5-Cl 3-cyano-4,6-dimethyl-2-pyridinyl 195-196 436 3-CF₃, 5-Cl 3,5-dichloro-6-dimethylamino-2-pyridinyl 238-239 437 3-CF₃, 5-Cl 3-iodo-6-methylamino-2-pyridinyl 156-157 438 — 2-bromo-5-(trifluoromethyl)phenyl >250 439 3-CF₃ 5-methoxy-2-methylphenyl 179-180 440 3-CF₃ 2-acetylamino-4-methyl-5-thiazolyl 248-249 445 3-CF₃, 5-CN 2,5-dimethylphenyl 202-203 446 3-CF₃, 5-Cl 6-dimethylamino-3-iodo-2-pyridinyl 179-180 447 3-CF₃, 5-C(O)NH₂ 4-cyano-2,5-dimethylphenyl >250 448 3-CF₃, 5-CN 2-cyano-5-(trifluoromethyl)phenyl * 449 3-CF₃ 2-chloro-5-ethoxyphenyl 224-225 451 3-CF₃, 5-SCH₂CH₃ 2-chloro-5-methoxyphenyl 195-196 455 3-CF₃, 5-Cl 5-(2-methoxyethyl)-2-thienyl 167-168 456 3-CF₃, 5-Cl 2-acetyl-3-thienyl 178-179 457 3-CF₃, 5-Cl 4-nitro-2-thienyl 192-193 458 3-CF₃, 5-CH₃ 2-chloro-5-(trifluoromethyl)phenyl 184-185 459 3-CF₃, 5-CH₃ 2,5-dimethylphenyl 235-236 460 3-CF₃ 2-chloro-5-methylphenyl 219-220 461 3-CF₃ 5-methyl-2-nitrophenyl >250 462 3-CF₃ 2-chloro-5-ethylphenyl 217-218 463 3-CF₃ 5-C(CH₃)₃-2-nitrophenyl 202-203 464 3-CF₃, 5-Cl 5-methyl-4-isoxazolyl 170-171 465 (Ex. 4) 3-CF₃, 5-Cl 1-ethyl-3-methyl-4-imidazolyl 189-190 466 3-CF₃ 1-ethyl-3-methyl-4-imidazolyl 148-149 467 3-CF₃ 5-bromo-2-chlorophenyl >250 468 3-CF₃ 2-bromo-5-(trifluoromethyl)phenyl >250 469 3-CF₃ 5-methoxy-2-nitrophenyl 228-229 470 3-CF₃ 5-acetyl-2-methylphenyl 206-207 471 3-CF₃ 2-bromo-5-propylphenyl 189-190 474 (Ex. 5) 3-CF₃, 5-Cl 3-chloro-1-ethyl-4-imidazolyl 184-185 475 3-CF₃, 5-Cl 3-chloro-1-isopropyl-4-imidazolyl 221-222 476 3-CF₃, 5-Cl 1-isopropyl-3-methyl-4-imidazolyl 163-164 R² is Br 317 3-CF₃, 5-Cl 2-fluorophenyl * 318 3-CF₃, 5-Cl 2-chloro-5-(trifluoromethyl)phenyl 582 402 3-CF₃, 5-Cl 2,5-dimethylphenyl 189-190 441 3-CF₃, 5-Cl 2-chloro-5-methoxyphenyl 202-203 442 3-CF₃, 5-Cl 3,5-dimethyl-4-isoxazolyl 194-195 443 3-CF₃, 5-Cl 4-cyano-5-methoxy-2-methylphenyl 232-233 444 3-CF₃, 5-Cl 4-cyano-2,5-dimethylphenyl 108-109 R² is CH₃ Cmpd (R¹)_(n) Q m.p. (° C.) 428 3-CF₃, 5-Cl 2,5-dimethylphenyl 191-192 429 3-CF₃, 5-Cl 2-chloro-5-(trifluoromethyl)phenyl 229-230 430 3-CF₃, 5-Cl 3,5-dimethyl-4-isoxazolyl 176-177 431 (Ex. 7) 3-CF₃, 5-Cl 2-chloro-5-methoxyphenyl 222-223 472 3-CF₃ 2-chloro-5-methoxyphenyl 222-223 473 3-CF₃ 2-bromo-5-propylphenyl 204-205 R² is CN 450 3-CF₃, 5-Cl 2,5-dimethylphenyl >250 R² is CH₂CH₃ 452 3-CF₃, 5-Cl 2,5-dimethylphenyl 202-203 453 3-CF₃, 5-Cl 2-chloro-5-(trifluoromethyl)phenyl 188-189 454 3-CF₃, 5-Cl 2-chloro-5-methoxyphenyl 161-162 * See Index Table E for ¹H NMR data.

INDEX TABLE C

Cmpd (R¹)_(n) R³ Q m.p. (° C.) 320 3-CF₃, 5-Cl CH₃ 4-methylphenyl * 321 3-Cl CH₃ 4-methylphenyl * 322 3-CF₃, 5-Cl CH₃ 2-chlorophenyl * 323 3-CF₃, 5-Cl CH₂CH₃ 2-chlorophenyl * 324 3-CF₃, 5-Cl CH₂CF₃ 2-chlorophenyl * 325 3-CF₃, 5-Cl CH₂C≡CH 2-chlorophenyl * 326 3-CF₃, 5-Cl CH₂CH═CH₂ 2-chlorophenyl * * See Index Table E for ¹H NMR data.

INDEX TABLE D m.p. Cmpd Structure (° C.) 328

* 477

>250 478

>250 479

185-186 * See Index Table E for ¹H NMR data.

INDEX TABLE E Cmpd No. ¹H NMR Data ^(a) 322 δ (acetone-d₆) 9.15 (s, 1H), 8.60 (s, 1H), 8.27 (d, 1H), 7.8-7.6 (m, 4H), 3.98 (s, 3H). 323 δ (acetone-d₆) 9.15 (s, 1H), 8.59 (s, 1H), 8.26 (d, 1H), 7.8-7.6 (m, 4H), 4.73 (q, 2H), 1.56 (t, 3H). 324 δ (acetone-d₆) 9.17 (s, 1H), 8.69 (s, 1H), 8.33 (d, 1H), 7.84 (s, 1H), 7.8-7.65 (m, 3H), 6.0 (br s, 2H). 325 δ (acetone-d₆) 9.18 (s, 1H), 8.66 (s, 1H), 8.30 (d, 1H), 7.8-7.6 (m, 4H), 5.71 (s, 2H), 2.83 (s, 1H). 326 δ (acetone-d₆) 9.14 (s, 1H), 8.59 (s, 1H), 8.30 (d, 1H), 7.8-7.6 (m, 4H), 6.2 (m, 1H), 5.46 (s, 2H), 5.4 (d, 1H), 5.2 (d, 1H). 108 δ (acetone-d₆) 11.25 (br s, 1H), 9.18 (s, 1H), 8.68 (s, 1H), 8.15 (t, 1H), 7.8 (m, 2H), 7.5 (t, 1H), 7.4 (dd, 1H). 140 δ (dmso-d₆) 9.29 (s, 1H), 8.72 (s, 1H), 7.97 (d, 1H), 7.64-7.48 (m, 3H), 7.29 (d, 1H), 3.88-3.78 (m, 3H). 319 δ (dmso-d₆) 9.33 (s, 1H), 8.79 (s, 1H), 8.40 (s, 1H), 8.11 (d, 1H), 7.96 (s, 2H). 278 δ (dmso-d₆) 9.03 (d, 1H), 8.65 (s, 1H), 8.37 (d, 1H), 8.09 (dd, 1H), 7.97 (d, 1H), 7.92 (d, 1H). 279 δ (dmso-d₆) 9.01 (s, 1H), 8.63 (s, 1H), 7.96 (s, 1H), 7.86 (s, 1H), 7.47-7.35 (m, 1H), 7.28 (d, 1H), 2.57 (s, 3H), 2.37 (s, 3H). 280 δ (dmso-d₆) 9.04-9.01 (m, 1H), 8.63 (s, 1H), 8.05 (dd, 1H), 7.97 (d, 1H), 7.86 (dd, 1H), 7.22 (dd, 1H). 281 δ (dmso-d₆) 8.98 (d, 1H), 8.58 (s, 1H), 7.97 (d, 1H), 7.67-7.48 (m, 3H), 7.27 (s, 1H), 3.83 (s, 3H). 284 δ (dmso-d₆) 9.47 (s, 1H), 8.58 (s, 1H), 8.35 (d, 1H), 7.99 (br s, 1H), 7.83 (br s, 3H). 289 δ (dmso-d₆) 9.23 (br s, 1H), 8.57 (s, 1H), 8.22 (br s, 2H), 7.93 (br s, 2H), 7.66 (br s, 3H), 7.33 (br s, 2H). 297 δ (dmso-d₆) 9.34 (s, 1H), 8.81 (s, 1H), 8.26 (d, 1H), 7.96 (d, 1H), 7.81 (d, 2H). 317 δ (dmso-d₆) 8.63 (d, 1H), 7.92 (d, 1H), 7.85 (m, 1H), 7.51-7.42 (m, 1H), 7.24 (m, 1H), 7.17 (d, 1H). 328 δ (dmso-d₆) 9.29 (s, 1H), 9.15 (s, 1H), 8.88 (s, 1H), 8.72 (s, 1H), 8.45-8.34 (m, 1H), 7.97 (d, 1H), 7.70 (dd, 1H). 251 δ 8.46 (s, 1H), 8.28 (s, 1H), 8.1 (s, 1H), 7.52 (s, 1H), 3.86 (s, 3H), 2.48 (s, 3H). 315 δ (dmso-d₆) 9.35 (d, 1H), 8.79 (s, 1H), 8.39 (d, 1H), 8.08 (s, 1H), 8.04 (d, 1H), 7.97 (s, 1H). 448 δ (dmso-d₆) 9.57 (br s, 1H), 8.73 (s, 1H), 8.48 (s, 1H), 8.34 (s, 1H), 8.23 (d, 1H), 8.13 (d, 1H), 7.96 (s, 1H). 320 δ 8.48 (m, 1H), 8.25 (s, 1H), 8.07 (m, 2H), 7.48 (m, 1H), 7.37) (m, 2H), 3.72 (s, 3H), 2.45 (s, 3H). 321 δ 8.16 (m, 1H), 8.07 (s, 1H), 7.99 (m, 2H), 7.57 (m, 2H), 7.34 (m, 2H), 7.23 (m, 1H), 3.80 (s, 3H), 2.43 (s, 3H). ^(a 1)H NMR data are in ppm downfield from tetramethylsilane. CDCl₃ solution unless indicated otherwise; “acetone-d₆” is CD₃C(═O)CD₃; “dmso-d₆” is CD₃S(═O)CD₃. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (m)-multiplet, (dd)-doublet of doublets, (br s)-broad singlet.

The following Tests demonstrate the control efficacy of compounds of this invention on specific pests. “Control efficacy” represents inhibition of parasitic nematode development (including mortality) that causes significantly reduced feeding. The pest control protection afforded by the compounds is not limited, however, to these species.

Biological Examples of the Invention Test A

Control of the southern root-knot nematode (Meloidogyne incognita) through contact and/or systemic means was evaluated in test units consisting of small open containers filled with a sandy soil mixture and cucumber seedlings.

Test compounds were formulated using a solution containing 50% acetone and 50% water. Test compounds were applied directly to the soil of the test units at concentrations of 250 or 50 ppm active ingredient. Each test was replicated 3 times. After treatment, the test units were allowed to dry for 1 hour, after which time about 250 second-stage juvenile (J2) larvae were pipetted into the soil. The test units were held at 27° C. and watered as needed for 7 days.

Nematocidal efficacy was determined by the amount of root gall formation observed when compared to an untreated control. No gall formation was indicative of 100% nematode control. Gall formation equivalent to that found in the untreated control was indicative of 0% control. No nematode control rating was given to compounds showing significant phytotoxicity.

Of the compounds tested at a concentration of 250 ppm, the following provided good levels of plant protection (50% or more reduction in root galling, compared to solvent-treated controls) and exhibited no significant phytotoxicity: 4, 5, 6, 7, 9, 10, 11, 12, 13, 17, 19, 24, 25, 28, 29, 30, 32, 34, 38, 57, 59, 63, 65, 66, 67, 68, 69, 70, 71, 72, 73, 75, 83, 89, 90, 93, 101, 106, 107, 108, 109, 110, 111, 112, 113, 114, 116, 117, 120, 126, 130, 131, 132, 133, 134, 136, 137, 139, 140, 143, 145, 149, 152, 157, 159, 162, 163, 167, 169, 170, 171, 172, 174, 175, 176, 179, 180, 181, 184, 186, 188, 193, 206, 241, 244, 245, 248, 251, 252, 253, 257, 258, 259, 272, 274, 279, 285, 292, 294, 297, 298, 299, 301, 313, 314, 315, 317, 318, 319, 323, 329, 331, 332, 333, 334, 340, 341, 342, 344, 345, 347, 348, 355, 359, 360, 361, 364, 365, 366, 367, 371, 372, 373, 375, 377, 378, 379, 380, 381, 382, 383, 384, 385, 386, 387, 388, 393, 394, 395, 396, 397, 402, 403, 404, 405, 406, 407, 408, 409, 410, 411, 412, 413, 414, 415, 417, 418, 419, 420, 421, 422, 424, 425, 426, 427, 429, 430, 436, 439, 441, 442, 443, 444, 445, 449, 450, 451, 458, 459, 460, 461, 462, 464, 465, 466, 467, 468, 469, 470, 471, 472, 474, 475, 476, 477, 478 and 479.

Of the compounds tested at a concentration of 50 ppm, the following provided good levels of plant protection (50% or more reduction in root galling, compared to solvent-treated controls) and exhibited no significant phytotoxicity: 2, 4, 7, 9, 10, 11, 13, 19, 30, 59, 63, 66, 67, 68, 69, 71, 73, 86, 90, 94, 101, 103, 105, 107, 108, 109, 110, 111, 113, 114, 116, 117, 130, 132, 133, 137, 139, 140, 143, 149, 151, 157, 162, 163, 167, 170, 175, 176, 179, 180, 241, 245, 248, 251, 252, 258, 259, 268, 272, 274, 279, 292, 297, 298, 314, 315, 316, 317, 318, 319, 329, 331, 332, 337, 341, 342, 343, 348, 356, 357, 359, 366, 367, 371, 372, 373, 377, 378, 379, 380, 381, 382, 383, 384, 386, 388, 394, 395, 396, 397, 401, 402, 403, 405, 406, 407, 408, 410, 411, 413, 414, 415, 416, 419, 420, 424, 427, 428, 429, 430, 431, 436, 439, 441, 442, 443, 444, 445, 449, 451, 458, 459, 460, 462, 465, 466, 467, 469, 470, 471, 474, 475, 477, 478 and 479. 

What is claimed is:
 1. A compound which is 8-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carbonyl chloride. 